fix(cli): suppress status lines in quiet mode

Status updates (searching, thinking, tool use) were printing to stderr
even with --quiet. Now gated behind !askQuiet so quiet mode is truly
non-streaming.

Co-Authored-By: Claude Opus 4.6 (1M context) <noreply@anthropic.com>

backend/alembic/versions/03d085c5c38d_backfill_account_type.py

@@ -0,0 +1,108 @@
+"""backfill_account_type
+
+Revision ID: 03d085c5c38d
+Revises: 977e834c1427
+Create Date: 2026-03-25 16:00:00.000000
+
+"""
+
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision = "03d085c5c38d"
+down_revision = "977e834c1427"
+branch_labels = None
+depends_on = None
+
+_STANDARD = "STANDARD"
+_BOT = "BOT"
+_EXT_PERM_USER = "EXT_PERM_USER"
+_SERVICE_ACCOUNT = "SERVICE_ACCOUNT"
+_ANONYMOUS = "ANONYMOUS"
+
+# Well-known anonymous user UUID
+ANONYMOUS_USER_ID = "00000000-0000-0000-0000-000000000002"
+
+# Email pattern for API key virtual users
+API_KEY_EMAIL_PATTERN = r"API\_KEY\_\_%"
+
+# Reflect the table structure for use in DML
+user_table = sa.table(
+    "user",
+    sa.column("id", sa.Uuid),
+    sa.column("email", sa.String),
+    sa.column("role", sa.String),
+    sa.column("account_type", sa.String),
+)
+
+
+def upgrade() -> None:
+    # ------------------------------------------------------------------
+    # Step 1: Backfill account_type from role.
+    # Order matters — most-specific matches first so the final catch-all
+    # only touches rows that haven't been classified yet.
+    # ------------------------------------------------------------------
+
+    # 1a. API key virtual users → SERVICE_ACCOUNT
+    op.execute(
+        sa.update(user_table)
+        .where(
+            user_table.c.email.ilike(API_KEY_EMAIL_PATTERN),
+            user_table.c.account_type.is_(None),
+        )
+        .values(account_type=_SERVICE_ACCOUNT)
+    )
+
+    # 1b. Anonymous user → ANONYMOUS
+    op.execute(
+        sa.update(user_table)
+        .where(
+            user_table.c.id == ANONYMOUS_USER_ID,
+            user_table.c.account_type.is_(None),
+        )
+        .values(account_type=_ANONYMOUS)
+    )
+
+    # 1c. SLACK_USER role → BOT
+    op.execute(
+        sa.update(user_table)
+        .where(
+            user_table.c.role == "SLACK_USER",
+            user_table.c.account_type.is_(None),
+        )
+        .values(account_type=_BOT)
+    )
+
+    # 1d. EXT_PERM_USER role → EXT_PERM_USER
+    op.execute(
+        sa.update(user_table)
+        .where(
+            user_table.c.role == "EXT_PERM_USER",
+            user_table.c.account_type.is_(None),
+        )
+        .values(account_type=_EXT_PERM_USER)
+    )
+
+    # 1e. Everything else → STANDARD
+    op.execute(
+        sa.update(user_table)
+        .where(user_table.c.account_type.is_(None))
+        .values(account_type=_STANDARD)
+    )
+
+    # ------------------------------------------------------------------
+    # Step 2: Set account_type to NOT NULL now that every row is filled.
+    # ------------------------------------------------------------------
+    op.alter_column(
+        "user",
+        "account_type",
+        nullable=False,
+        server_default="STANDARD",
+    )
+
+
+def downgrade() -> None:
+    op.alter_column("user", "account_type", nullable=True, server_default=None)
+    op.execute(sa.update(user_table).values(account_type=None))

backend/alembic/versions/503883791c39_add_effective_permissions.py

@@ -0,0 +1,104 @@
+"""add_effective_permissions
+
+Adds a JSONB column `effective_permissions` to the user table to store
+directly granted permissions (e.g. ["admin"] or ["basic"]). Implied
+permissions are expanded at read time, not stored.
+
+Backfill: joins user__user_group → permission_grant to collect each
+user's granted permissions into a JSON array. Users without group
+memberships keep the default [].
+
+Revision ID: 503883791c39
+Revises: b4b7e1028dfd
+Create Date: 2026-03-30 14:49:22.261748
+
+"""
+
+from collections.abc import Sequence
+
+from alembic import op
+import sqlalchemy as sa
+from sqlalchemy.dialects import postgresql
+
+
+# revision identifiers, used by Alembic.
+revision = "503883791c39"
+down_revision = "b4b7e1028dfd"
+branch_labels: str | None = None
+depends_on: str | Sequence[str] | None = None
+
+user_table = sa.table(
+    "user",
+    sa.column("id", sa.Uuid),
+    sa.column("effective_permissions", postgresql.JSONB),
+)
+
+user_user_group = sa.table(
+    "user__user_group",
+    sa.column("user_id", sa.Uuid),
+    sa.column("user_group_id", sa.Integer),
+)
+
+permission_grant = sa.table(
+    "permission_grant",
+    sa.column("group_id", sa.Integer),
+    sa.column("permission", sa.String),
+    sa.column("is_deleted", sa.Boolean),
+)
+
+
+def upgrade() -> None:
+    op.add_column(
+        "user",
+        sa.Column(
+            "effective_permissions",
+            postgresql.JSONB(),
+            nullable=False,
+            server_default=sa.text("'[]'::jsonb"),
+        ),
+    )
+
+    conn = op.get_bind()
+
+    # Deduplicated permissions per user
+    deduped = (
+        sa.select(
+            user_user_group.c.user_id,
+            permission_grant.c.permission,
+        )
+        .select_from(
+            user_user_group.join(
+                permission_grant,
+                sa.and_(
+                    permission_grant.c.group_id == user_user_group.c.user_group_id,
+                    permission_grant.c.is_deleted == sa.false(),
+                ),
+            )
+        )
+        .distinct()
+        .subquery("deduped")
+    )
+
+    # Aggregate into JSONB array per user (order is not guaranteed;
+    # consumers read this as a set so ordering does not matter)
+    perms_per_user = (
+        sa.select(
+            deduped.c.user_id,
+            sa.func.jsonb_agg(
+                deduped.c.permission,
+                type_=postgresql.JSONB,
+            ).label("perms"),
+        )
+        .group_by(deduped.c.user_id)
+        .subquery("sub")
+    )
+
+    conn.execute(
+        user_table.update()
+        .where(user_table.c.id == perms_per_user.c.user_id)
+        .values(effective_permissions=perms_per_user.c.perms)
+    )
+
+
+def downgrade() -> None:
+    op.drop_column("user", "effective_permissions")

backend/alembic/versions/977e834c1427_seed_default_groups.py

@@ -0,0 +1,139 @@
+"""seed_default_groups
+
+Revision ID: 977e834c1427
+Revises: 8188861f4e92
+Create Date: 2026-03-25 14:59:41.313091
+
+"""
+
+from typing import Any
+
+from alembic import op
+import sqlalchemy as sa
+from sqlalchemy.dialects.postgresql import insert as pg_insert
+
+
+# revision identifiers, used by Alembic.
+revision = "977e834c1427"
+down_revision = "8188861f4e92"
+branch_labels = None
+depends_on = None
+
+# (group_name, permission_value)
+DEFAULT_GROUPS = [
+    ("Admin", "admin"),
+    ("Basic", "basic"),
+]
+
+CUSTOM_SUFFIX = "(Custom)"
+
+MAX_RENAME_ATTEMPTS = 100
+
+# Reflect table structures for use in DML
+user_group_table = sa.table(
+    "user_group",
+    sa.column("id", sa.Integer),
+    sa.column("name", sa.String),
+    sa.column("is_up_to_date", sa.Boolean),
+    sa.column("is_up_for_deletion", sa.Boolean),
+    sa.column("is_default", sa.Boolean),
+)
+
+permission_grant_table = sa.table(
+    "permission_grant",
+    sa.column("group_id", sa.Integer),
+    sa.column("permission", sa.String),
+    sa.column("grant_source", sa.String),
+)
+
+user__user_group_table = sa.table(
+    "user__user_group",
+    sa.column("user_group_id", sa.Integer),
+    sa.column("user_id", sa.Uuid),
+)
+
+
+def _find_available_name(conn: sa.engine.Connection, base: str) -> str:
+    """Return a name like 'Admin (Custom)' or 'Admin (Custom 2)' that is not taken."""
+    candidate = f"{base} {CUSTOM_SUFFIX}"
+    attempt = 1
+    while attempt <= MAX_RENAME_ATTEMPTS:
+        exists: Any = conn.execute(
+            sa.select(sa.literal(1))
+            .select_from(user_group_table)
+            .where(user_group_table.c.name == candidate)
+            .limit(1)
+        ).fetchone()
+        if exists is None:
+            return candidate
+        attempt += 1
+        candidate = f"{base} (Custom {attempt})"
+    raise RuntimeError(
+        f"Could not find an available name for group '{base}' "
+        f"after {MAX_RENAME_ATTEMPTS} attempts"
+    )
+
+
+def upgrade() -> None:
+    conn = op.get_bind()
+
+    for group_name, permission_value in DEFAULT_GROUPS:
+        # Step 1: Rename ALL existing groups that clash with the canonical name.
+        conflicting = conn.execute(
+            sa.select(user_group_table.c.id, user_group_table.c.name).where(
+                user_group_table.c.name == group_name
+            )
+        ).fetchall()
+
+        for row_id, row_name in conflicting:
+            new_name = _find_available_name(conn, row_name)
+            op.execute(
+                sa.update(user_group_table)
+                .where(user_group_table.c.id == row_id)
+                .values(name=new_name, is_up_to_date=False)
+            )
+
+        # Step 2: Create a fresh default group.
+        result = conn.execute(
+            user_group_table.insert()
+            .values(
+                name=group_name,
+                is_up_to_date=True,
+                is_up_for_deletion=False,
+                is_default=True,
+            )
+            .returning(user_group_table.c.id)
+        ).fetchone()
+        assert result is not None
+        group_id = result[0]
+
+        # Step 3: Upsert permission grant.
+        op.execute(
+            pg_insert(permission_grant_table)
+            .values(
+                group_id=group_id,
+                permission=permission_value,
+                grant_source="SYSTEM",
+            )
+            .on_conflict_do_nothing(index_elements=["group_id", "permission"])
+        )
+
+
+def downgrade() -> None:
+    # Remove the default groups created by this migration.
+    # First remove user-group memberships that reference default groups
+    # to avoid FK violations, then delete the groups themselves.
+    default_group_ids = sa.select(user_group_table.c.id).where(
+        user_group_table.c.is_default == True  # noqa: E712
+    )
+    conn = op.get_bind()
+    conn.execute(
+        sa.delete(user__user_group_table).where(
+            user__user_group_table.c.user_group_id.in_(default_group_ids)
+        )
+    )
+    conn.execute(
+        sa.delete(user_group_table).where(
+            user_group_table.c.is_default == True  # noqa: E712
+        )
+    )

backend/alembic/versions/b4b7e1028dfd_grant_basic_to_existing_groups.py

@@ -0,0 +1,84 @@
+"""grant_basic_to_existing_groups
+
+Grants the "basic" permission to all existing groups that don't already
+have it. Every group should have at least "basic" so that its members
+get basic access when effective_permissions is backfilled.
+
+Revision ID: b4b7e1028dfd
+Revises: b7bcc991d722
+Create Date: 2026-03-30 16:15:17.093498
+
+"""
+
+from collections.abc import Sequence
+
+from alembic import op
+import sqlalchemy as sa
+
+
+# revision identifiers, used by Alembic.
+revision = "b4b7e1028dfd"
+down_revision = "b7bcc991d722"
+branch_labels: str | None = None
+depends_on: str | Sequence[str] | None = None
+
+user_group = sa.table(
+    "user_group",
+    sa.column("id", sa.Integer),
+    sa.column("is_default", sa.Boolean),
+)
+
+permission_grant = sa.table(
+    "permission_grant",
+    sa.column("group_id", sa.Integer),
+    sa.column("permission", sa.String),
+    sa.column("grant_source", sa.String),
+    sa.column("is_deleted", sa.Boolean),
+)
+
+
+def upgrade() -> None:
+    conn = op.get_bind()
+
+    already_has_basic = (
+        sa.select(sa.literal(1))
+        .select_from(permission_grant)
+        .where(
+            permission_grant.c.group_id == user_group.c.id,
+            permission_grant.c.permission == "basic",
+        )
+        .exists()
+    )
+
+    groups_needing_basic = sa.select(
+        user_group.c.id,
+        sa.literal("basic").label("permission"),
+        sa.literal("SYSTEM").label("grant_source"),
+        sa.literal(False).label("is_deleted"),
+    ).where(
+        user_group.c.is_default == sa.false(),
+        ~already_has_basic,
+    )
+
+    conn.execute(
+        permission_grant.insert().from_select(
+            ["group_id", "permission", "grant_source", "is_deleted"],
+            groups_needing_basic,
+        )
+    )
+
+
+def downgrade() -> None:
+    conn = op.get_bind()
+
+    non_default_group_ids = sa.select(user_group.c.id).where(
+        user_group.c.is_default == sa.false()
+    )
+
+    conn.execute(
+        permission_grant.delete().where(
+            permission_grant.c.permission == "basic",
+            permission_grant.c.grant_source == "SYSTEM",
+            permission_grant.c.group_id.in_(non_default_group_ids),
+        )
+    )

backend/alembic/versions/b7bcc991d722_assign_users_to_default_groups.py

@@ -0,0 +1,125 @@
+"""assign_users_to_default_groups
+
+Revision ID: b7bcc991d722
+Revises: 03d085c5c38d
+Create Date: 2026-03-25 16:30:39.529301
+
+"""
+
+from alembic import op
+import sqlalchemy as sa
+from sqlalchemy.dialects.postgresql import insert as pg_insert
+
+
+# revision identifiers, used by Alembic.
+revision = "b7bcc991d722"
+down_revision = "03d085c5c38d"
+branch_labels = None
+depends_on = None
+
+# The no-auth placeholder user must NOT be assigned to default groups.
+# A database trigger (migrate_no_auth_data_to_user) will try to DELETE this
+# user when the first real user registers; group membership rows would cause
+# an FK violation on that DELETE.
+NO_AUTH_PLACEHOLDER_USER_UUID = "00000000-0000-0000-0000-000000000001"
+
+# Reflect table structures for use in DML
+user_group_table = sa.table(
+    "user_group",
+    sa.column("id", sa.Integer),
+    sa.column("name", sa.String),
+    sa.column("is_default", sa.Boolean),
+)
+
+user_table = sa.table(
+    "user",
+    sa.column("id", sa.Uuid),
+    sa.column("role", sa.String),
+    sa.column("account_type", sa.String),
+    sa.column("is_active", sa.Boolean),
+)
+
+user__user_group_table = sa.table(
+    "user__user_group",
+    sa.column("user_group_id", sa.Integer),
+    sa.column("user_id", sa.Uuid),
+)
+
+
+def upgrade() -> None:
+    conn = op.get_bind()
+
+    # Look up default group IDs
+    admin_row = conn.execute(
+        sa.select(user_group_table.c.id).where(
+            user_group_table.c.name == "Admin",
+            user_group_table.c.is_default == True,  # noqa: E712
+        )
+    ).fetchone()
+
+    basic_row = conn.execute(
+        sa.select(user_group_table.c.id).where(
+            user_group_table.c.name == "Basic",
+            user_group_table.c.is_default == True,  # noqa: E712
+        )
+    ).fetchone()
+
+    if admin_row is None:
+        raise RuntimeError(
+            "Default 'Admin' group not found. "
+            "Ensure migration 977e834c1427 (seed_default_groups) ran successfully."
+        )
+
+    if basic_row is None:
+        raise RuntimeError(
+            "Default 'Basic' group not found. "
+            "Ensure migration 977e834c1427 (seed_default_groups) ran successfully."
+        )
+
+    # Users with role=admin → Admin group
+    # Include inactive users so reactivation doesn't require reconciliation.
+    # Exclude non-human account types (mirrors assign_user_to_default_groups logic).
+    admin_users = sa.select(
+        sa.literal(admin_row[0]).label("user_group_id"),
+        user_table.c.id.label("user_id"),
+    ).where(
+        user_table.c.role == "ADMIN",
+        user_table.c.account_type.notin_(["BOT", "EXT_PERM_USER", "ANONYMOUS"]),
+        user_table.c.id != NO_AUTH_PLACEHOLDER_USER_UUID,
+    )
+    op.execute(
+        pg_insert(user__user_group_table)
+        .from_select(["user_group_id", "user_id"], admin_users)
+        .on_conflict_do_nothing(index_elements=["user_group_id", "user_id"])
+    )
+
+    # STANDARD users (non-admin) and SERVICE_ACCOUNT users (role=basic) → Basic group
+    # Include inactive users so reactivation doesn't require reconciliation.
+    basic_users = sa.select(
+        sa.literal(basic_row[0]).label("user_group_id"),
+        user_table.c.id.label("user_id"),
+    ).where(
+        user_table.c.account_type.notin_(["BOT", "EXT_PERM_USER", "ANONYMOUS"]),
+        user_table.c.id != NO_AUTH_PLACEHOLDER_USER_UUID,
+        sa.or_(
+            sa.and_(
+                user_table.c.account_type == "STANDARD",
+                user_table.c.role != "ADMIN",
+            ),
+            sa.and_(
+                user_table.c.account_type == "SERVICE_ACCOUNT",
+                user_table.c.role == "BASIC",
+            ),
+        ),
+    )
+    op.execute(
+        pg_insert(user__user_group_table)
+        .from_select(["user_group_id", "user_id"], basic_users)
+        .on_conflict_do_nothing(index_elements=["user_group_id", "user_id"])
+    )
+
+
+def downgrade() -> None:
+    # Group memberships are left in place — removing them risks
+    # deleting memberships that existed before this migration.
+    pass

backend/ee/onyx/db/scim.py

@@ -36,13 +36,16 @@ from ee.onyx.server.scim.filtering import ScimFilter
 from ee.onyx.server.scim.filtering import ScimFilterOperator
 from ee.onyx.server.scim.models import ScimMappingFields
 from onyx.db.dal import DAL
+from onyx.db.enums import AccountType
+from onyx.db.enums import GrantSource
+from onyx.db.enums import Permission
+from onyx.db.models import PermissionGrant
 from onyx.db.models import ScimGroupMapping
 from onyx.db.models import ScimToken
 from onyx.db.models import ScimUserMapping
 from onyx.db.models import User
 from onyx.db.models import User__UserGroup
 from onyx.db.models import UserGroup
-from onyx.db.models import UserRole
 from onyx.utils.logger import setup_logger
 
 logger = setup_logger()
@@ -280,7 +283,9 @@ class ScimDAL(DAL):
         query = (
             select(User)
             .join(ScimUserMapping, ScimUserMapping.user_id == User.id)
-            .where(User.role.notin_([UserRole.SLACK_USER, UserRole.EXT_PERM_USER]))
+            .where(
+                User.account_type.notin_([AccountType.BOT, AccountType.EXT_PERM_USER])
+            )
         )
 
         if scim_filter:
@@ -521,6 +526,22 @@ class ScimDAL(DAL):
         self._session.add(group)
         self._session.flush()
 
+    def add_permission_grant_to_group(
+        self,
+        group_id: int,
+        permission: Permission,
+        grant_source: GrantSource,
+    ) -> None:
+        """Grant a permission to a group and flush."""
+        self._session.add(
+            PermissionGrant(
+                group_id=group_id,
+                permission=permission,
+                grant_source=grant_source,
+            )
+        )
+        self._session.flush()
+
     def update_group(
         self,
         group: UserGroup,

backend/ee/onyx/db/user_group.py

@@ -19,6 +19,8 @@ from onyx.configs.app_configs import DISABLE_VECTOR_DB
 from onyx.db.connector_credential_pair import get_connector_credential_pair_from_id
 from onyx.db.enums import AccessType
 from onyx.db.enums import ConnectorCredentialPairStatus
+from onyx.db.enums import GrantSource
+from onyx.db.enums import Permission
 from onyx.db.models import ConnectorCredentialPair
 from onyx.db.models import Credential
 from onyx.db.models import Credential__UserGroup
@@ -28,6 +30,7 @@ from onyx.db.models import DocumentSet
 from onyx.db.models import DocumentSet__UserGroup
 from onyx.db.models import FederatedConnector__DocumentSet
 from onyx.db.models import LLMProvider__UserGroup
+from onyx.db.models import PermissionGrant
 from onyx.db.models import Persona
 from onyx.db.models import Persona__UserGroup
 from onyx.db.models import TokenRateLimit__UserGroup
@@ -36,6 +39,7 @@ from onyx.db.models import User__UserGroup
 from onyx.db.models import UserGroup
 from onyx.db.models import UserGroup__ConnectorCredentialPair
 from onyx.db.models import UserRole
+from onyx.db.permissions import recompute_user_permissions__no_commit
 from onyx.db.users import fetch_user_by_id
 from onyx.utils.logger import setup_logger
 
@@ -255,6 +259,7 @@ def fetch_user_groups(
     db_session: Session,
     only_up_to_date: bool = True,
     eager_load_for_snapshot: bool = False,
+    include_default: bool = True,
 ) -> Sequence[UserGroup]:
     """
     Fetches user groups from the database.
@@ -269,6 +274,7 @@ def fetch_user_groups(
             to include only up to date user groups. Defaults to `True`.
         eager_load_for_snapshot: If True, adds eager loading for all relationships
             needed by UserGroup.from_model snapshot creation.
+        include_default: If False, excludes system default groups (is_default=True).
 
     Returns:
         Sequence[UserGroup]: A sequence of `UserGroup` objects matching the query criteria.
@@ -276,6 +282,8 @@ def fetch_user_groups(
     stmt = select(UserGroup)
     if only_up_to_date:
         stmt = stmt.where(UserGroup.is_up_to_date == True)  # noqa: E712
+    if not include_default:
+        stmt = stmt.where(UserGroup.is_default == False)  # noqa: E712
     if eager_load_for_snapshot:
         stmt = _add_user_group_snapshot_eager_loads(stmt)
     return db_session.scalars(stmt).unique().all()
@@ -286,6 +294,7 @@ def fetch_user_groups_for_user(
     user_id: UUID,
     only_curator_groups: bool = False,
     eager_load_for_snapshot: bool = False,
+    include_default: bool = True,
 ) -> Sequence[UserGroup]:
     stmt = (
         select(UserGroup)
@@ -295,6 +304,8 @@ def fetch_user_groups_for_user(
     )
     if only_curator_groups:
         stmt = stmt.where(User__UserGroup.is_curator == True)  # noqa: E712
+    if not include_default:
+        stmt = stmt.where(UserGroup.is_default == False)  # noqa: E712
     if eager_load_for_snapshot:
         stmt = _add_user_group_snapshot_eager_loads(stmt)
     return db_session.scalars(stmt).unique().all()
@@ -478,6 +489,16 @@ def insert_user_group(db_session: Session, user_group: UserGroupCreate) -> UserG
     db_session.add(db_user_group)
     db_session.flush()  # give the group an ID
 
+    # Every group gets the "basic" permission by default
+    db_session.add(
+        PermissionGrant(
+            group_id=db_user_group.id,
+            permission=Permission.BASIC_ACCESS,
+            grant_source=GrantSource.SYSTEM,
+        )
+    )
+    db_session.flush()
+
     _add_user__user_group_relationships__no_commit(
         db_session=db_session,
         user_group_id=db_user_group.id,
@@ -489,6 +510,8 @@ def insert_user_group(db_session: Session, user_group: UserGroupCreate) -> UserG
         cc_pair_ids=user_group.cc_pair_ids,
     )
 
+    recompute_user_permissions__no_commit(user_group.user_ids, db_session)
+
     db_session.commit()
     return db_user_group
 
@@ -796,6 +819,10 @@ def update_user_group(
     # update "time_updated" to now
     db_user_group.time_last_modified_by_user = func.now()
 
+    recompute_user_permissions__no_commit(
+        list(set(added_user_ids) | set(removed_user_ids)), db_session
+    )
+
     db_session.commit()
     return db_user_group
 
@@ -835,6 +862,19 @@ def prepare_user_group_for_deletion(db_session: Session, user_group_id: int) ->
 
     _check_user_group_is_modifiable(db_user_group)
 
+    # Collect affected user IDs before cleanup deletes the relationships
+    affected_user_ids: list[UUID] = [
+        uid
+        for uid in db_session.execute(
+            select(User__UserGroup.user_id).where(
+                User__UserGroup.user_group_id == user_group_id
+            )
+        )
+        .scalars()
+        .all()
+        if uid is not None
+    ]
+
     _mark_user_group__cc_pair_relationships_outdated__no_commit(
         db_session=db_session, user_group_id=user_group_id
     )
@@ -863,6 +903,10 @@ def prepare_user_group_for_deletion(db_session: Session, user_group_id: int) ->
         db_session=db_session, user_group_id=user_group_id
     )
 
+    # Recompute permissions for affected users now that their
+    # membership in this group has been removed
+    recompute_user_permissions__no_commit(affected_user_ids, db_session)
+
     db_user_group.is_up_to_date = False
     db_user_group.is_up_for_deletion = True
     db_session.commit()

backend/ee/onyx/server/scim/api.py

@@ -52,16 +52,25 @@ from ee.onyx.server.scim.schema_definitions import SERVICE_PROVIDER_CONFIG
 from ee.onyx.server.scim.schema_definitions import USER_RESOURCE_TYPE
 from ee.onyx.server.scim.schema_definitions import USER_SCHEMA_DEF
 from onyx.db.engine.sql_engine import get_session
+from onyx.db.enums import AccountType
+from onyx.db.enums import GrantSource
+from onyx.db.enums import Permission
 from onyx.db.models import ScimToken
 from onyx.db.models import ScimUserMapping
 from onyx.db.models import User
 from onyx.db.models import UserGroup
 from onyx.db.models import UserRole
+from onyx.db.permissions import recompute_permissions_for_group__no_commit
+from onyx.db.permissions import recompute_user_permissions__no_commit
+from onyx.db.users import assign_user_to_default_groups__no_commit
 from onyx.utils.logger import setup_logger
 from onyx.utils.variable_functionality import fetch_ee_implementation_or_noop
 
 logger = setup_logger()
 
+# Group names reserved for system default groups (seeded by migration).
+_RESERVED_GROUP_NAMES = frozenset({"Admin", "Basic"})
+
 
 class ScimJSONResponse(JSONResponse):
     """JSONResponse with Content-Type: application/scim+json (RFC 7644 §3.1)."""
@@ -486,6 +495,7 @@ def create_user(
         email=email,
         hashed_password=_pw_helper.hash(_pw_helper.generate()),
         role=UserRole.BASIC,
+        account_type=AccountType.STANDARD,
         is_active=user_resource.active,
         is_verified=True,
         personal_name=personal_name,
@@ -506,13 +516,25 @@ def create_user(
             scim_username=scim_username,
             fields=fields,
         )
-        dal.commit()
     except IntegrityError:
         dal.rollback()
         return _scim_error_response(
             409, f"User with email {email} already has a SCIM mapping"
         )
 
+    # Assign user to default group BEFORE commit so everything is atomic.
+    # If this fails, the entire user creation rolls back and IdP can retry.
+    try:
+        assign_user_to_default_groups__no_commit(db_session, user)
+    except Exception:
+        dal.rollback()
+        logger.exception(f"Failed to assign SCIM user {email} to default groups")
+        return _scim_error_response(
+            500, f"Failed to assign user {email} to default group"
+        )
+
+    dal.commit()
+
     return _scim_resource_response(
         provider.build_user_resource(
             user,
@@ -542,7 +564,8 @@ def replace_user(
     user = result
 
     # Handle activation (need seat check) / deactivation
-    if user_resource.active and not user.is_active:
+    is_reactivation = user_resource.active and not user.is_active
+    if is_reactivation:
         seat_error = _check_seat_availability(dal)
         if seat_error:
             return _scim_error_response(403, seat_error)
@@ -556,6 +579,12 @@ def replace_user(
         personal_name=personal_name,
     )
 
+    # Reconcile default-group membership on reactivation
+    if is_reactivation:
+        assign_user_to_default_groups__no_commit(
+            db_session, user, is_admin=(user.role == UserRole.ADMIN)
+        )
+
     new_external_id = user_resource.externalId
     scim_username = user_resource.userName.strip()
     fields = _fields_from_resource(user_resource)
@@ -621,6 +650,7 @@ def patch_user(
         return _scim_error_response(e.status, e.detail)
 
     # Apply changes back to the DB model
+    is_reactivation = patched.active and not user.is_active
     if patched.active != user.is_active:
         if patched.active:
             seat_error = _check_seat_availability(dal)
@@ -649,6 +679,12 @@ def patch_user(
         personal_name=personal_name,
     )
 
+    # Reconcile default-group membership on reactivation
+    if is_reactivation:
+        assign_user_to_default_groups__no_commit(
+            db_session, user, is_admin=(user.role == UserRole.ADMIN)
+        )
+
     # Build updated fields by merging PATCH enterprise data with current values
     cf = current_fields or ScimMappingFields()
     fields = ScimMappingFields(
@@ -857,6 +893,11 @@ def create_group(
     dal = ScimDAL(db_session)
     dal.update_token_last_used(_token.id)
 
+    if group_resource.displayName in _RESERVED_GROUP_NAMES:
+        return _scim_error_response(
+            409, f"'{group_resource.displayName}' is a reserved group name."
+        )
+
     if dal.get_group_by_name(group_resource.displayName):
         return _scim_error_response(
             409, f"Group with name '{group_resource.displayName}' already exists"
@@ -879,8 +920,18 @@ def create_group(
             409, f"Group with name '{group_resource.displayName}' already exists"
         )
 
+    # Every group gets the "basic" permission by default.
+    dal.add_permission_grant_to_group(
+        group_id=db_group.id,
+        permission=Permission.BASIC_ACCESS,
+        grant_source=GrantSource.SYSTEM,
+    )
+
     dal.upsert_group_members(db_group.id, member_uuids)
 
+    # Recompute permissions for initial members.
+    recompute_user_permissions__no_commit(member_uuids, db_session)
+
     external_id = group_resource.externalId
     if external_id:
         dal.create_group_mapping(external_id=external_id, user_group_id=db_group.id)
@@ -911,14 +962,36 @@ def replace_group(
         return result
     group = result
 
+    if group.name in _RESERVED_GROUP_NAMES and group_resource.displayName != group.name:
+        return _scim_error_response(
+            409, f"'{group.name}' is a reserved group name and cannot be renamed."
+        )
+
+    if (
+        group_resource.displayName in _RESERVED_GROUP_NAMES
+        and group_resource.displayName != group.name
+    ):
+        return _scim_error_response(
+            409, f"'{group_resource.displayName}' is a reserved group name."
+        )
+
     member_uuids, err = _validate_and_parse_members(group_resource.members, dal)
     if err:
         return _scim_error_response(400, err)
 
+    # Capture old member IDs before replacing so we can recompute their
+    # permissions after they are removed from the group.
+    old_member_ids = {uid for uid, _ in dal.get_group_members(group.id)}
+
     dal.update_group(group, name=group_resource.displayName)
     dal.replace_group_members(group.id, member_uuids)
     dal.sync_group_external_id(group.id, group_resource.externalId)
 
+    # Recompute permissions for current members (batch) and removed members.
+    recompute_permissions_for_group__no_commit(group.id, db_session)
+    removed_ids = list(old_member_ids - set(member_uuids))
+    recompute_user_permissions__no_commit(removed_ids, db_session)
+
     dal.commit()
 
     members = dal.get_group_members(group.id)
@@ -961,8 +1034,19 @@ def patch_group(
         return _scim_error_response(e.status, e.detail)
 
     new_name = patched.displayName if patched.displayName != group.name else None
+
+    if group.name in _RESERVED_GROUP_NAMES and new_name:
+        return _scim_error_response(
+            409, f"'{group.name}' is a reserved group name and cannot be renamed."
+        )
+
+    if new_name and new_name in _RESERVED_GROUP_NAMES:
+        return _scim_error_response(409, f"'{new_name}' is a reserved group name.")
+
     dal.update_group(group, name=new_name)
 
+    affected_uuids: list[UUID] = []
+
     if added_ids:
         add_uuids = [UUID(mid) for mid in added_ids if _is_valid_uuid(mid)]
         if add_uuids:
@@ -973,10 +1057,15 @@ def patch_group(
                     f"Member(s) not found: {', '.join(str(u) for u in missing)}",
                 )
             dal.upsert_group_members(group.id, add_uuids)
+            affected_uuids.extend(add_uuids)
 
     if removed_ids:
         remove_uuids = [UUID(mid) for mid in removed_ids if _is_valid_uuid(mid)]
         dal.remove_group_members(group.id, remove_uuids)
+        affected_uuids.extend(remove_uuids)
+
+    # Recompute permissions for all users whose group membership changed.
+    recompute_user_permissions__no_commit(affected_uuids, db_session)
 
     dal.sync_group_external_id(group.id, patched.externalId)
     dal.commit()
@@ -1002,11 +1091,21 @@ def delete_group(
         return result
     group = result
 
+    if group.name in _RESERVED_GROUP_NAMES:
+        return _scim_error_response(409, f"'{group.name}' is a reserved group name.")
+
+    # Capture member IDs before deletion so we can recompute their permissions.
+    affected_user_ids = [uid for uid, _ in dal.get_group_members(group.id)]
+
     mapping = dal.get_group_mapping_by_group_id(group.id)
     if mapping:
         dal.delete_group_mapping(mapping.id)
 
     dal.delete_group_with_members(group)
+
+    # Recompute permissions for users who lost this group membership.
+    recompute_user_permissions__no_commit(affected_user_ids, db_session)
+
     dal.commit()
 
     return Response(status_code=204)

backend/ee/onyx/server/user_group/api.py

@@ -43,12 +43,16 @@ router = APIRouter(prefix="/manage", tags=PUBLIC_API_TAGS)
 
 @router.get("/admin/user-group")
 def list_user_groups(
+    include_default: bool = False,
     user: User = Depends(current_curator_or_admin_user),
     db_session: Session = Depends(get_session),
 ) -> list[UserGroup]:
     if user.role == UserRole.ADMIN:
         user_groups = fetch_user_groups(
-            db_session, only_up_to_date=False, eager_load_for_snapshot=True
+            db_session,
+            only_up_to_date=False,
+            eager_load_for_snapshot=True,
+            include_default=include_default,
         )
     else:
         user_groups = fetch_user_groups_for_user(
@@ -56,27 +60,50 @@ def list_user_groups(
             user_id=user.id,
             only_curator_groups=user.role == UserRole.CURATOR,
             eager_load_for_snapshot=True,
+            include_default=include_default,
         )
     return [UserGroup.from_model(user_group) for user_group in user_groups]
 
 
 @router.get("/user-groups/minimal")
 def list_minimal_user_groups(
+    include_default: bool = False,
     user: User = Depends(current_user),
     db_session: Session = Depends(get_session),
 ) -> list[MinimalUserGroupSnapshot]:
     if user.role == UserRole.ADMIN:
-        user_groups = fetch_user_groups(db_session, only_up_to_date=False)
+        user_groups = fetch_user_groups(
+            db_session,
+            only_up_to_date=False,
+            include_default=include_default,
+        )
     else:
         user_groups = fetch_user_groups_for_user(
             db_session=db_session,
             user_id=user.id,
+            include_default=include_default,
         )
     return [
         MinimalUserGroupSnapshot.from_model(user_group) for user_group in user_groups
     ]
 
 
+@router.get("/admin/user-group/{user_group_id}/permissions")
+def get_user_group_permissions(
+    user_group_id: int,
+    _: User = Depends(current_admin_user),
+    db_session: Session = Depends(get_session),
+) -> list[str]:
+    group = fetch_user_group(db_session, user_group_id)
+    if group is None:
+        raise OnyxError(OnyxErrorCode.NOT_FOUND, "User group not found")
+    return [
+        grant.permission.value
+        for grant in group.permission_grants
+        if not grant.is_deleted
+    ]
+
+
 @router.post("/admin/user-group")
 def create_user_group(
     user_group: UserGroupCreate,
@@ -100,6 +127,9 @@ def rename_user_group_endpoint(
     _: User = Depends(current_admin_user),
     db_session: Session = Depends(get_session),
 ) -> UserGroup:
+    group = fetch_user_group(db_session, rename_request.id)
+    if group and group.is_default:
+        raise OnyxError(OnyxErrorCode.CONFLICT, "Cannot rename a default system group.")
     try:
         return UserGroup.from_model(
             rename_user_group(
@@ -185,6 +215,9 @@ def delete_user_group(
     _: User = Depends(current_admin_user),
     db_session: Session = Depends(get_session),
 ) -> None:
+    group = fetch_user_group(db_session, user_group_id)
+    if group and group.is_default:
+        raise OnyxError(OnyxErrorCode.CONFLICT, "Cannot delete a default system group.")
     try:
         prepare_user_group_for_deletion(db_session, user_group_id)
     except ValueError as e:

backend/ee/onyx/server/user_group/models.py

@@ -22,6 +22,7 @@ class UserGroup(BaseModel):
     personas: list[PersonaSnapshot]
     is_up_to_date: bool
     is_up_for_deletion: bool
+    is_default: bool
 
     @classmethod
     def from_model(cls, user_group_model: UserGroupModel) -> "UserGroup":
@@ -74,18 +75,21 @@ class UserGroup(BaseModel):
             ],
             is_up_to_date=user_group_model.is_up_to_date,
             is_up_for_deletion=user_group_model.is_up_for_deletion,
+            is_default=user_group_model.is_default,
         )
 
 
 class MinimalUserGroupSnapshot(BaseModel):
     id: int
     name: str
+    is_default: bool
 
     @classmethod
     def from_model(cls, user_group_model: UserGroupModel) -> "MinimalUserGroupSnapshot":
         return cls(
             id=user_group_model.id,
             name=user_group_model.name,
+            is_default=user_group_model.is_default,
         )
 
 

backend/onyx/auth/permissions.py

@@ -0,0 +1,110 @@
+"""
+Permission resolution for group-based authorization.
+
+Granted permissions are stored as a JSONB column on the User table and
+loaded for free with every auth query. Implied permissions are expanded
+at read time — only directly granted permissions are persisted.
+"""
+
+from collections.abc import Callable
+from collections.abc import Coroutine
+from typing import Any
+
+from fastapi import Depends
+
+from onyx.auth.users import current_user
+from onyx.db.enums import Permission
+from onyx.db.models import User
+from onyx.error_handling.error_codes import OnyxErrorCode
+from onyx.error_handling.exceptions import OnyxError
+from onyx.utils.logger import setup_logger
+
+logger = setup_logger()
+
+ALL_PERMISSIONS: frozenset[str] = frozenset(p.value for p in Permission)
+
+# Implication map: granted permission -> set of permissions it implies.
+IMPLIED_PERMISSIONS: dict[str, set[str]] = {
+    Permission.ADD_AGENTS.value: {Permission.READ_AGENTS.value},
+    Permission.MANAGE_AGENTS.value: {
+        Permission.ADD_AGENTS.value,
+        Permission.READ_AGENTS.value,
+    },
+    Permission.MANAGE_DOCUMENT_SETS.value: {
+        Permission.READ_DOCUMENT_SETS.value,
+        Permission.READ_CONNECTORS.value,
+    },
+    Permission.ADD_CONNECTORS.value: {Permission.READ_CONNECTORS.value},
+    Permission.MANAGE_CONNECTORS.value: {
+        Permission.ADD_CONNECTORS.value,
+        Permission.READ_CONNECTORS.value,
+    },
+    Permission.MANAGE_USER_GROUPS.value: {
+        Permission.READ_CONNECTORS.value,
+        Permission.READ_DOCUMENT_SETS.value,
+        Permission.READ_AGENTS.value,
+        Permission.READ_USERS.value,
+    },
+}
+
+
+def resolve_effective_permissions(granted: set[str]) -> set[str]:
+    """Expand granted permissions with their implied permissions.
+
+    If "admin" is present, returns all 19 permissions.
+    """
+    if Permission.FULL_ADMIN_PANEL_ACCESS.value in granted:
+        return set(ALL_PERMISSIONS)
+
+    effective = set(granted)
+    changed = True
+    while changed:
+        changed = False
+        for perm in list(effective):
+            implied = IMPLIED_PERMISSIONS.get(perm)
+            if implied and not implied.issubset(effective):
+                effective |= implied
+                changed = True
+    return effective
+
+
+def get_effective_permissions(user: User) -> set[Permission]:
+    """Read granted permissions from the column and expand implied permissions."""
+    granted: set[Permission] = set()
+    for p in user.effective_permissions:
+        try:
+            granted.add(Permission(p))
+        except ValueError:
+            logger.warning(f"Skipping unknown permission '{p}' for user {user.id}")
+    if Permission.FULL_ADMIN_PANEL_ACCESS in granted:
+        return set(Permission)
+    expanded = resolve_effective_permissions({p.value for p in granted})
+    return {Permission(p) for p in expanded}
+
+
+def require_permission(
+    required: Permission,
+) -> Callable[..., Coroutine[Any, Any, User]]:
+    """FastAPI dependency factory for permission-based access control.
+
+    Usage:
+        @router.get("/endpoint")
+        def endpoint(user: User = Depends(require_permission(Permission.MANAGE_CONNECTORS))):
+            ...
+    """
+
+    async def dependency(user: User = Depends(current_user)) -> User:
+        effective = get_effective_permissions(user)
+
+        if Permission.FULL_ADMIN_PANEL_ACCESS in effective:
+            return user
+
+        if required not in effective:
+            raise OnyxError(
+                OnyxErrorCode.INSUFFICIENT_PERMISSIONS,
+                "You do not have the required permissions for this action.",
+            )
+
+        return user
+
+    return dependency

backend/onyx/auth/schemas.py

@@ -5,6 +5,8 @@ from typing import Any
 from fastapi_users import schemas
 from typing_extensions import override
 
+from onyx.db.enums import AccountType
+
 
 class UserRole(str, Enum):
     """
@@ -41,6 +43,7 @@ class UserRead(schemas.BaseUser[uuid.UUID]):
 
 class UserCreate(schemas.BaseUserCreate):
     role: UserRole = UserRole.BASIC
+    account_type: AccountType = AccountType.STANDARD
     tenant_id: str | None = None
     # Captcha token for cloud signup protection (optional, only used when captcha is enabled)
     # Excluded from create_update_dict so it never reaches the DB layer
@@ -50,19 +53,19 @@ class UserCreate(schemas.BaseUserCreate):
     def create_update_dict(self) -> dict[str, Any]:
         d = super().create_update_dict()
         d.pop("captcha_token", None)
+        # Force STANDARD for self-registration; only trusted paths
+        # (SCIM, API key creation) supply a different account_type directly.
+        d["account_type"] = AccountType.STANDARD
         return d
 
     @override
     def create_update_dict_superuser(self) -> dict[str, Any]:
         d = super().create_update_dict_superuser()
         d.pop("captcha_token", None)
+        d.setdefault("account_type", self.account_type)
         return d
 
 
-class UserUpdateWithRole(schemas.BaseUserUpdate):
-    role: UserRole
-
-
 class UserUpdate(schemas.BaseUserUpdate):
     """
     Role updates are not allowed through the user update endpoint for security reasons

backend/onyx/auth/users.py

@@ -80,7 +80,6 @@ from onyx.auth.pat import get_hashed_pat_from_request
 from onyx.auth.schemas import AuthBackend
 from onyx.auth.schemas import UserCreate
 from onyx.auth.schemas import UserRole
-from onyx.auth.schemas import UserUpdateWithRole
 from onyx.configs.app_configs import AUTH_BACKEND
 from onyx.configs.app_configs import AUTH_COOKIE_EXPIRE_TIME_SECONDS
 from onyx.configs.app_configs import AUTH_TYPE
@@ -120,11 +119,13 @@ from onyx.db.engine.async_sql_engine import get_async_session
 from onyx.db.engine.async_sql_engine import get_async_session_context_manager
 from onyx.db.engine.sql_engine import get_session_with_current_tenant
 from onyx.db.engine.sql_engine import get_session_with_tenant
+from onyx.db.enums import AccountType
 from onyx.db.models import AccessToken
 from onyx.db.models import OAuthAccount
 from onyx.db.models import Persona
 from onyx.db.models import User
 from onyx.db.pat import fetch_user_for_pat
+from onyx.db.users import assign_user_to_default_groups__no_commit
 from onyx.db.users import get_user_by_email
 from onyx.error_handling.error_codes import OnyxErrorCode
 from onyx.error_handling.exceptions import log_onyx_error
@@ -500,18 +501,21 @@ class UserManager(UUIDIDMixin, BaseUserManager[User, uuid.UUID]):
                             user = user_by_session
 
                     if (
-                        user.role.is_web_login()
+                        user.account_type.is_web_login()
                         or not isinstance(user_create, UserCreate)
-                        or not user_create.role.is_web_login()
+                        or not user_create.account_type.is_web_login()
                     ):
                         raise exceptions.UserAlreadyExists()
 
-                    user_update = UserUpdateWithRole(
-                        password=user_create.password,
-                        is_verified=user_create.is_verified,
-                        role=user_create.role,
-                    )
-                    user = await self.update(user_update, user)
+                    # Cache id before expire — accessing attrs on an expired
+                    # object triggers a sync lazy-load which raises MissingGreenlet
+                    # in this async context.
+                    user_id = user.id
+                    self._upgrade_user_to_standard__sync(user_id, user_create)
+                    # Expire so the async session re-fetches the row updated by
+                    # the sync session above.
+                    self.user_db.session.expire(user)
+                    user = await self.user_db.get(user_id)  # type: ignore[assignment]
                 except exceptions.UserAlreadyExists:
                     user = await self.get_by_email(user_create.email)
 
@@ -525,18 +529,21 @@ class UserManager(UUIDIDMixin, BaseUserManager[User, uuid.UUID]):
 
                     # Handle case where user has used product outside of web and is now creating an account through web
                     if (
-                        user.role.is_web_login()
+                        user.account_type.is_web_login()
                         or not isinstance(user_create, UserCreate)
-                        or not user_create.role.is_web_login()
+                        or not user_create.account_type.is_web_login()
                     ):
                         raise exceptions.UserAlreadyExists()
 
-                    user_update = UserUpdateWithRole(
-                        password=user_create.password,
-                        is_verified=user_create.is_verified,
-                        role=user_create.role,
-                    )
-                    user = await self.update(user_update, user)
+                    # Cache id before expire — accessing attrs on an expired
+                    # object triggers a sync lazy-load which raises MissingGreenlet
+                    # in this async context.
+                    user_id = user.id
+                    self._upgrade_user_to_standard__sync(user_id, user_create)
+                    # Expire so the async session re-fetches the row updated by
+                    # the sync session above.
+                    self.user_db.session.expire(user)
+                    user = await self.user_db.get(user_id)  # type: ignore[assignment]
                 if user_created:
                     await self._assign_default_pinned_assistants(user, db_session)
                 remove_user_from_invited_users(user_create.email)
@@ -573,6 +580,38 @@ class UserManager(UUIDIDMixin, BaseUserManager[User, uuid.UUID]):
         )
         user.pinned_assistants = default_persona_ids
 
+    def _upgrade_user_to_standard__sync(
+        self,
+        user_id: uuid.UUID,
+        user_create: UserCreate,
+    ) -> None:
+        """Upgrade a non-web user to STANDARD and assign default groups atomically.
+
+        All writes happen in a single sync transaction so neither the field
+        update nor the group assignment is visible without the other.
+        """
+        with get_session_with_current_tenant() as sync_db:
+            sync_user = sync_db.query(User).filter(User.id == user_id).first()  # type: ignore[arg-type]
+            if sync_user:
+                sync_user.hashed_password = self.password_helper.hash(
+                    user_create.password
+                )
+                sync_user.is_verified = user_create.is_verified or False
+                sync_user.role = user_create.role
+                sync_user.account_type = AccountType.STANDARD
+                assign_user_to_default_groups__no_commit(
+                    sync_db,
+                    sync_user,
+                    is_admin=(user_create.role == UserRole.ADMIN),
+                )
+                sync_db.commit()
+            else:
+                logger.warning(
+                    "User %s not found in sync session during upgrade to standard; "
+                    "skipping upgrade",
+                    user_id,
+                )
+
     async def validate_password(self, password: str, _: schemas.UC | models.UP) -> None:
         # Validate password according to configurable security policy (defined via environment variables)
         if len(password) < PASSWORD_MIN_LENGTH:
@@ -694,6 +733,7 @@ class UserManager(UUIDIDMixin, BaseUserManager[User, uuid.UUID]):
                         "email": account_email,
                         "hashed_password": self.password_helper.hash(password),
                         "is_verified": is_verified_by_default,
+                        "account_type": AccountType.STANDARD,
                     }
 
                     user = await self.user_db.create(user_dict)
@@ -726,7 +766,7 @@ class UserManager(UUIDIDMixin, BaseUserManager[User, uuid.UUID]):
                 )
 
             # Handle case where user has used product outside of web and is now creating an account through web
-            if not user.role.is_web_login():
+            if not user.account_type.is_web_login():
                 # We must use the existing user in the session if it matches
                 # the user we just got by email/oauth. Note that this only applies
                 # to multi-tenant, due to the overwriting of the user_db
@@ -743,14 +783,25 @@ class UserManager(UUIDIDMixin, BaseUserManager[User, uuid.UUID]):
                     with get_session_with_current_tenant() as sync_db:
                         enforce_seat_limit(sync_db)
 
-                await self.user_db.update(
-                    user,
-                    {
-                        "is_verified": is_verified_by_default,
-                        "role": UserRole.BASIC,
-                        **({"is_active": True} if not user.is_active else {}),
-                    },
-                )
+                # Upgrade the user and assign default groups in a single
+                # transaction so neither change is visible without the other.
+                was_inactive = not user.is_active
+                with get_session_with_current_tenant() as sync_db:
+                    sync_user = sync_db.query(User).filter(User.id == user.id).first()  # type: ignore[arg-type]
+                    if sync_user:
+                        sync_user.is_verified = is_verified_by_default
+                        sync_user.role = UserRole.BASIC
+                        sync_user.account_type = AccountType.STANDARD
+                        if was_inactive:
+                            sync_user.is_active = True
+                        assign_user_to_default_groups__no_commit(sync_db, sync_user)
+                        sync_db.commit()
+
+                # Refresh the async user object so downstream code
+                # (e.g. oidc_expiry check) sees the updated fields.
+                self.user_db.session.expire(user)
+                user = await self.user_db.get(user.id)
+                assert user is not None
 
             # this is needed if an organization goes from `TRACK_EXTERNAL_IDP_EXPIRY=true` to `false`
             # otherwise, the oidc expiry will always be old, and the user will never be able to login
@@ -836,6 +887,16 @@ class UserManager(UUIDIDMixin, BaseUserManager[User, uuid.UUID]):
                     event=MilestoneRecordType.TENANT_CREATED,
                 )
 
+            # Assign user to the appropriate default group (Admin or Basic).
+            # Must happen inside the try block while tenant context is active,
+            # otherwise get_session_with_current_tenant() targets the wrong schema.
+            is_admin = user_count == 1 or user.email in get_default_admin_user_emails()
+            with get_session_with_current_tenant() as db_session:
+                assign_user_to_default_groups__no_commit(
+                    db_session, user, is_admin=is_admin
+                )
+                db_session.commit()
+
         finally:
             CURRENT_TENANT_ID_CONTEXTVAR.reset(token)
 
@@ -975,7 +1036,7 @@ class UserManager(UUIDIDMixin, BaseUserManager[User, uuid.UUID]):
                 self.password_helper.hash(credentials.password)
                 return None
 
-            if not user.role.is_web_login():
+            if not user.account_type.is_web_login():
                 raise BasicAuthenticationError(
                     detail="NO_WEB_LOGIN_AND_HAS_NO_PASSWORD",
                 )
@@ -1471,7 +1532,7 @@ async def _get_or_create_user_from_jwt(
         if not user.is_active:
             logger.warning("Inactive user %s attempted JWT login; skipping", email)
             return None
-        if not user.role.is_web_login():
+        if not user.account_type.is_web_login():
             raise exceptions.UserNotExists()
     except exceptions.UserNotExists:
         logger.info("Provisioning user %s from JWT login", email)
@@ -1492,7 +1553,7 @@ async def _get_or_create_user_from_jwt(
                     email,
                 )
                 return None
-            if not user.role.is_web_login():
+            if not user.account_type.is_web_login():
                 logger.warning(
                     "Non-web-login user %s attempted JWT login during provisioning race; skipping",
                     email,
@@ -1554,6 +1615,7 @@ def get_anonymous_user() -> User:
         is_verified=True,
         is_superuser=False,
         role=UserRole.LIMITED,
+        account_type=AccountType.ANONYMOUS,
         use_memories=False,
         enable_memory_tool=False,
     )

backend/onyx/chat/README.md

@@ -1,5 +1,10 @@
 # Overview of Context Management
 
+This document reviews some design decisions around the main agent-loop powering Onyx's chat flow.
+It is highly recommended for all engineers contributing to this flow to be familiar with the concepts here.
+
+> Note: it is assumed the reader is familiar with the Onyx product and features such as Projects, User files, Citations, etc. 
+
 ## System Prompt
 
 The system prompt is a default prompt that comes packaged with the system. Users can edit the default prompt and it will be persisted in the database.
@@ -41,9 +46,9 @@ the system can RAG over the project files.
 
 ## How documents are represented
 
-Documents from search or uploaded Project files are represented as a json so that the LLM can easily understand it. It is represented with a prefix to make the
-context clearer to the LLM. Note that for search results (whether web or internal, it will just be the json) and it will be a Tool Call type of message
-rather than a user message.
+Documents from search or uploaded Project files are represented as a json so that the LLM can easily understand it. It is represented with a prefix string to
+make the context clearer to the LLM. Note that for search results (whether web or internal, it will just be the json) and it will be a Tool Call type of
+message rather than a user message.
 
 ```
 Here are some documents provided for context, they may not all be relevant:
@@ -55,12 +60,12 @@ Here are some documents provided for context, they may not all be relevant:
 }
 ```
 
-Documents are represented with document so that the LLM can easily cite them with a single number. The tool returns have to be richer to be able to
+Documents are represented with the `document` key so that the LLM can easily cite them with a single number. The tool returns have to be richer to be able to
 translate this into links and other UI elements. What the LLM sees is far simpler to reduce noise/hallucinations.
 
 Note that documents included in a single turn should be collapsed into a single user message.
 
-Search tools give URLs to the LLM though so that open_url (a separate tool) can be called on them.
+Search tools also give URLs to the LLM so that open_url (a separate tool) can be called on them.
 
 ## Reminders
 
@@ -72,10 +77,13 @@ If a search related tool is called at any point during the turn, the reminder wi
 
 ## Tool Calls
 
-As tool call responses can get very long (like an internal search can be many thousands of tokens), tool responses are today replaced with a hardcoded
+As tool call responses can get very long (like an internal search can be many thousands of tokens), tool responses are current replaced with a hardcoded
 string saying it is no longer available. Tool Call details like the search query and other arguments are kept in the history as this is information
 rich and generally very few tokens.
 
+> Note: in the Internal Search flow with query expansion, the Tool Call which was actually run differs from what the LLM provided as arguments.
+> What the LLM sees in the history (to be most informative for future calls) is the full set of expanded queries.
+
 **Possible Future Extension**:
 Instead of dropping the Tool Call response, we might summarize it using an LLM so that it is just 1-2 sentences and captures the main points. That said,
 this is questionable value add because anything relevant and useful should be already captured in the Agent response.
@@ -103,7 +111,7 @@ Flow with Project and File Upload
 S, CA, P, F, U1, A1 -- user sends another message -> S, F, U1, A1, CA, P, U2, A2
 - File stays in place, above the user message
 - Project files move along the chain as new messages are sent
-- Custom Agent prompt comes before project files which comes before user uploaded files in each turn
+- Custom Agent prompt comes before project files which come before user uploaded files in each turn
 
 Reminders during a single Turn
 S, U1, TC, TR, R -- agent calls another tool -> S, U1, TC, TR, TC, TR, R, A1
@@ -124,7 +132,7 @@ and should be very targetted for it to work reliably and also not interfere with
 
 ## Reasons / Experiments
 
-Custom Agent instructions being placed in the system prompt is poorly followed. It also degrade performance of the system especially when the instructions
+Custom Agent instructions being placed in the system prompt is poorly followed. It also degrades performance of the system especially when the instructions
 are orthogonal (or even possibly contradictory) to the system prompt. For weaker models, it causes strange artifacts in tool calls and final responses
 that completely ruins the user experience. Empirically, this way works better across a range of models especially when the history gets longer.
 Having the Custom Agent instructions not move means it fades more as the chat gets long which is also not ok from a UX perspective.
@@ -151,7 +159,7 @@ In a similar concept, LLM instructions in the system prompt are structured speci
 fairly surprising actually but if there is a line of instructions effectively saying "If you try to use some tools and find that you need more information or
 need to call additional tools, you are encouraged to do this", having this in the Tool section of the System prompt makes all the LLMs follow it well but if it's
 even just a paragraph away like near the beginning of the prompt, it is often ignored. The difference is as drastic as a 30% follow rate to a 90% follow
-rate even just moving the same statement a few sentences.
+rate by even just moving the same statement a few sentences.
 
 ## Other related pointers
 
@@ -235,8 +243,9 @@ tool calls and returns that to the LLM Loop to execute.
   concept of a turn. The turn_index for the frontend is which block does this packet belong to. So while a reasoning + tool call
   comes from the same LLM inference (same backend LLM step), they are 2 turns to the frontend because that's how it's rendered.
 
-- There are 3 representations of "message". The first is the database model ChatMessage, this one should be translated away and
-  not used deep into the flow. The second is ChatMessageSimple which is the data model which should be used throughout the code
-  as much as possible. If modifications/additions are needed, it should be to this object. This is the rich representation of a
-  message for the code. Finally there is the LanguageModelInput representation of a message. This one is for the LLM interface
-  layer and is as stripped down as possible so that the LLM interface can be clean and easy to maintain/extend.
+- There are 3 representations of a message, each scoped to a different layer:
+  1. **ChatMessage** — The database model. Should be converted into ChatMessageSimple early and never passed deep into the flow.
+  2. **ChatMessageSimple** — The canonical data model used throughout the codebase. This is the rich, full-featured representation
+     of a message. Any modifications or additions to message structure should be made here.
+  3. **LanguageModelInput** — The LLM-facing representation. Intentionally minimal so the LLM interface layer stays clean and
+     easy to maintain/extend.

backend/onyx/chat/emitter.py

@@ -30,7 +30,7 @@ class Emitter:
         self._drain_done = drain_done
 
     def emit(self, packet: Packet) -> None:
-        if self._drain_done and self._drain_done.is_set():
+        if self._drain_done is not None and self._drain_done.is_set():
             return
         base = packet.placement or Placement(turn_index=0)
         tagged = Packet(

backend/onyx/chat/process_message.py

@@ -3,7 +3,7 @@ IMPORTANT: familiarize yourself with the design concepts prior to contributing t
 An overview can be found in the README.md file in this directory.
 """
 
-import functools
+import contextvars
 import io
 import queue
 import re
@@ -11,7 +11,9 @@ import threading
 import traceback
 from collections.abc import Callable
 from collections.abc import Generator
+from concurrent.futures import ThreadPoolExecutor
 from contextvars import Token
+from typing import Final
 from uuid import UUID
 
 from sqlalchemy.orm import Session
@@ -64,6 +66,7 @@ from onyx.db.chat import create_new_chat_message
 from onyx.db.chat import get_chat_session_by_id
 from onyx.db.chat import get_or_create_root_message
 from onyx.db.chat import reserve_message_id
+from onyx.db.chat import reserve_multi_model_message_ids
 from onyx.db.engine.sql_engine import get_session_with_current_tenant
 from onyx.db.enums import HookPoint
 from onyx.db.memory import get_memories
@@ -91,6 +94,7 @@ from onyx.llm.factory import get_llm_for_persona
 from onyx.llm.factory import get_llm_token_counter
 from onyx.llm.interfaces import LLM
 from onyx.llm.interfaces import LLMUserIdentity
+from onyx.llm.override_models import LLMOverride
 from onyx.llm.request_context import reset_llm_mock_response
 from onyx.llm.request_context import set_llm_mock_response
 from onyx.llm.utils import litellm_exception_to_error_msg
@@ -98,6 +102,8 @@ from onyx.onyxbot.slack.models import SlackContext
 from onyx.server.query_and_chat.chat_utils import mime_type_to_chat_file_type
 from onyx.server.query_and_chat.models import AUTO_PLACE_AFTER_LATEST_MESSAGE
 from onyx.server.query_and_chat.models import MessageResponseIDInfo
+from onyx.server.query_and_chat.models import ModelResponseSlot
+from onyx.server.query_and_chat.models import MultiModelMessageResponseIDInfo
 from onyx.server.query_and_chat.models import SendMessageRequest
 from onyx.server.query_and_chat.placement import Placement
 from onyx.server.query_and_chat.streaming_models import AgentResponseDelta
@@ -116,13 +122,11 @@ from onyx.tools.tool_constructor import FileReaderToolConfig
 from onyx.tools.tool_constructor import SearchToolConfig
 from onyx.utils.logger import setup_logger
 from onyx.utils.telemetry import mt_cloud_telemetry
-from onyx.utils.threadpool_concurrency import run_multiple_in_background
 from onyx.utils.timing import log_function_time
 from shared_configs.contextvars import get_current_tenant_id
 
 logger = setup_logger()
 ERROR_TYPE_CANCELLED = "cancelled"
-
 APPROX_CHARS_PER_TOKEN = 4
 
 
@@ -482,6 +486,8 @@ def build_chat_turn(
     new_msg_req: SendMessageRequest,
     user: User,
     db_session: Session,
+    # None → single-model (persona default LLM); non-empty list → multi-model (one LLM per override)
+    llm_overrides: list[LLMOverride] | None,
     *,
     litellm_additional_headers: dict[str, str] | None = None,
     custom_tool_additional_headers: dict[str, str] | None = None,
@@ -494,21 +500,23 @@ def build_chat_turn(
     # NOTE: not stored in the database, only passed in to the LLM as context
     additional_context: str | None = None,
 ) -> Generator[AnswerStreamPart, None, ChatTurnSetup]:
-    """Setup generator for a single-model chat turn.
+    """Shared setup generator for both single-model and multi-model chat turns.
 
     Yields the packet(s) the frontend needs for request tracking, then returns an
     immutable ``ChatTurnSetup`` containing everything the execution strategy needs.
 
     Callers use::
 
-        setup = yield from build_chat_turn(new_msg_req, ...)
+        setup = yield from build_chat_turn(new_msg_req, ..., llm_overrides=...)
 
     to forward yielded packets upstream while receiving the return value locally.
+
+    Args:
+        llm_overrides: ``None`` → single-model (persona default LLM).
+                       Non-empty list → multi-model (one LLM per override).
     """
-    # TODO(nmgarza5): Consider refactoring so that yields move to handle_stream_message_objects
-    # and build_chat_turn becomes a plain function returning ChatTurnSetup. This would make
-    # the generator pattern (yield from build_chat_turn) unnecessary and easier to reason about.
     tenant_id = get_current_tenant_id()
+    is_multi = bool(llm_overrides)
 
     user_id = user.id
     llm_user_identifier = (
@@ -519,22 +527,25 @@ def build_chat_turn(
     if not new_msg_req.chat_session_id:
         if not new_msg_req.chat_session_info:
             raise RuntimeError("Must specify a chat session id or chat session info")
-        new_session = create_chat_session_from_request(
+        chat_session = create_chat_session_from_request(
             chat_session_request=new_msg_req.chat_session_info,
             user_id=user_id,
             db_session=db_session,
         )
-        session_id = new_session.id
-        yield CreateChatSessionID(chat_session_id=session_id)
+        yield CreateChatSessionID(chat_session_id=chat_session.id)
+        chat_session = get_chat_session_by_id(
+            chat_session_id=chat_session.id,
+            user_id=user_id,
+            db_session=db_session,
+            eager_load_persona=True,
+        )
     else:
-        session_id = new_msg_req.chat_session_id
-
-    chat_session = get_chat_session_by_id(
-        chat_session_id=session_id,
-        user_id=user_id,
-        db_session=db_session,
-        eager_load_persona=True,
-    )
+        chat_session = get_chat_session_by_id(
+            chat_session_id=new_msg_req.chat_session_id,
+            user_id=user_id,
+            db_session=db_session,
+            eager_load_persona=True,
+        )
 
     persona = chat_session.persona
     message_text = new_msg_req.message
@@ -563,21 +574,33 @@ def build_chat_turn(
     )
 
     # Check LLM cost limits before using the LLM (only for Onyx-managed keys),
-    # then build the LLM instance.
-    primary_llm = get_llm_for_persona(
-        persona=persona,
-        user=user,
-        llm_override=new_msg_req.llm_override or chat_session.llm_override,
-        additional_headers=litellm_additional_headers,
+    # then build the LLM instance(s).
+    llms: list[LLM] = []
+    model_display_names: list[str] = []
+    selected_overrides: list[LLMOverride | None] = (
+        list(llm_overrides or [])
+        if is_multi
+        else [new_msg_req.llm_override or chat_session.llm_override]
     )
-    check_llm_cost_limit_for_provider(
-        db_session=db_session,
-        tenant_id=tenant_id,
-        llm_provider_api_key=primary_llm.config.api_key,
-    )
-    llms = [primary_llm]
-    model_display_names = [""]
-    token_counter = get_llm_token_counter(primary_llm)
+    for override in selected_overrides:
+        llm = get_llm_for_persona(
+            persona=persona,
+            user=user,
+            llm_override=override,
+            additional_headers=litellm_additional_headers,
+        )
+        check_llm_cost_limit_for_provider(
+            db_session=db_session,
+            tenant_id=tenant_id,
+            llm_provider_api_key=llm.config.api_key,
+        )
+        llms.append(llm)
+        model_display_names.append(_build_model_display_name(override))
+    token_counter = get_llm_token_counter(llms[0])
+
+    # not sure why we do this, but to maintain parity with previous code:
+    if not is_multi:
+        model_display_names = [""]
 
     # Verify that the user-specified files actually belong to the user
     verify_user_files(
@@ -738,7 +761,8 @@ def build_chat_turn(
         db_session=db_session,
     )
 
-    llm_max_context_window = llms[0].config.max_input_tokens
+    # Use the smallest context window across models for safety (harmless for N=1).
+    llm_max_context_window = min(llm.config.max_input_tokens for llm in llms)
 
     extracted_context_files = extract_context_files(
         user_files=context_user_files,
@@ -782,18 +806,34 @@ def build_chat_turn(
     # Convert loaded files to ChatFile format for tools like PythonTool
     chat_files_for_tools = _convert_loaded_files_to_chat_files(files)
 
-    # ── Reserve assistant message ID → yield to frontend ─────────────────────
-    assistant_response = reserve_message_id(
-        db_session=db_session,
-        chat_session_id=chat_session.id,
-        parent_message=user_message.id,
-        message_type=MessageType.ASSISTANT,
-    )
-    reserved_messages = [assistant_response]
-    yield MessageResponseIDInfo(
-        user_message_id=user_message.id,
-        reserved_assistant_message_id=assistant_response.id,
-    )
+    # ── Reserve assistant message ID(s) → yield to frontend ──────────────────
+    if is_multi:
+        assert llm_overrides is not None
+        reserved_messages = reserve_multi_model_message_ids(
+            db_session=db_session,
+            chat_session_id=chat_session.id,
+            parent_message_id=user_message.id,
+            model_display_names=model_display_names,
+        )
+        yield MultiModelMessageResponseIDInfo(
+            user_message_id=user_message.id,
+            responses=[
+                ModelResponseSlot(message_id=m.id, model_name=name)
+                for m, name in zip(reserved_messages, model_display_names)
+            ],
+        )
+    else:
+        assistant_response = reserve_message_id(
+            db_session=db_session,
+            chat_session_id=chat_session.id,
+            parent_message=user_message.id,
+            message_type=MessageType.ASSISTANT,
+        )
+        reserved_messages = [assistant_response]
+        yield MessageResponseIDInfo(
+            user_message_id=user_message.id,
+            reserved_assistant_message_id=assistant_response.id,
+        )
 
     # Convert the chat history into a simple format that is free of any DB objects
     # and is easy to parse for the agent loop.
@@ -896,6 +936,9 @@ def build_chat_turn(
 # Sentinel placed on the merged queue when a model thread finishes.
 _MODEL_DONE = object()
 
+# How often the drain loop polls for user-initiated cancellation (stop button).
+_CANCEL_POLL_INTERVAL_S: Final[float] = 0.05
+
 
 def _run_models(
     setup: ChatTurnSetup,
@@ -906,7 +949,7 @@ def _run_models(
     """Stream packets from one or more LLM loops running in parallel worker threads.
 
     Each model gets its own worker thread, DB session, and ``Emitter``. Threads write
-    packets to a shared bounded queue as they are produced; the drain loop yields them
+    packets to a shared unbounded queue as they are produced; the drain loop yields them
     in arrival order so the caller receives a single interleaved stream regardless of
     how many models are running.
 
@@ -934,8 +977,6 @@ def _run_models(
 
     merged_queue: queue.Queue[tuple[int, Packet | Exception | object]] = queue.Queue()
 
-    # external_state_container is only non-None for single-model turns (n_models == 1),
-    # so only index 0 can receive it. Multi-model turns always create fresh containers.
     state_containers: list[ChatStateContainer] = [
         (
             external_state_container
@@ -945,9 +986,12 @@ def _run_models(
         for i in range(n_models)
     ]
     model_succeeded: list[bool] = [False] * n_models
+    # Set to True when a model raises an exception (distinct from "still running").
+    # Used in the stop-button path to avoid calling completion for errored models.
+    model_errored: list[bool] = [False] * n_models
 
     # Set when the drain loop exits early (HTTP disconnect / GeneratorExit).
-    # Signals emitters to skip future puts and workers to self-complete.
+    # Signals emitters to skip future puts so workers exit promptly.
     drain_done = threading.Event()
 
     def _run_model(model_idx: int) -> None:
@@ -1052,85 +1096,84 @@ def _run_models(
             model_succeeded[model_idx] = True
 
         except Exception as e:
+            model_errored[model_idx] = True
             merged_queue.put((model_idx, e))
 
         finally:
             merged_queue.put((model_idx, _MODEL_DONE))
 
-        # Self-completion on disconnect: _MODEL_DONE was already posted in the finally
-        # block above, so the drain loop has counted this model. If drain_done is set,
-        # the main thread exited early and will NOT call llm_loop_completion_handle for
-        # this model — open a fresh session and persist the response here instead.
-        if drain_done.is_set() and model_succeeded[model_idx]:
-            try:
-                with get_session_with_current_tenant() as self_complete_db:
-                    assistant_message = self_complete_db.get(
-                        ChatMessage, setup.reserved_messages[model_idx].id
-                    )
-                    if assistant_message is not None:
-                        llm_loop_completion_handle(
-                            state_container=state_containers[model_idx],
-                            # Guard on line above already ensures model_succeeded is True.
-                            is_connected=lambda: True,
-                            db_session=self_complete_db,
-                            assistant_message=assistant_message,
-                            llm=setup.llms[model_idx],
-                            reserved_tokens=setup.reserved_token_count,
-                        )
-            except Exception:
-                logger.exception(
-                    "model %d (%s): self-completion after disconnect failed",
-                    model_idx,
-                    setup.model_display_names[model_idx],
-                )
+    def _delete_orphaned_message(model_idx: int, context: str) -> None:
+        """Delete a reserved ChatMessage that was never populated due to a model error."""
+        try:
+            orphaned = db_session.get(
+                ChatMessage, setup.reserved_messages[model_idx].id
+            )
+            if orphaned is not None:
+                db_session.delete(orphaned)
+                db_session.commit()
+        except Exception:
+            logger.exception(
+                "%s orphan cleanup failed for model %d (%s)",
+                context,
+                model_idx,
+                setup.model_display_names[model_idx],
+            )
 
-    executor = run_multiple_in_background(
-        [functools.partial(_run_model, i) for i in range(n_models)],
-        thread_name_prefix="multi-model",
+    # Copy contextvars before submitting futures — ThreadPoolExecutor does NOT
+    # auto-propagate contextvars in Python 3.11; threads would inherit a blank context.
+    worker_context = contextvars.copy_context()
+    executor = ThreadPoolExecutor(
+        max_workers=n_models, thread_name_prefix="multi-model"
     )
-    _completion_done: bool = False
+    completion_persisted: bool = False
     try:
+        for i in range(n_models):
+            executor.submit(worker_context.run, _run_model, i)
+
         # ── Main thread: merge and yield packets ────────────────────────────
         models_remaining = n_models
-        last_turn_index = 0
         while models_remaining > 0:
             try:
-                model_idx, item = merged_queue.get(timeout=0.05)
+                model_idx, item = merged_queue.get(timeout=_CANCEL_POLL_INTERVAL_S)
             except queue.Empty:
                 # Check for user-initiated cancellation every 50 ms.
-                if setup.check_is_connected():
-                    continue
-
-                # Save state for every model before exiting. Models that already
-                # finished (model_succeeded[i]=True) get their full answer saved;
-                # models still in-flight get partial answer + "stopped by user".
-                for i in range(n_models):
-                    try:
-                        llm_loop_completion_handle(
-                            state_container=state_containers[i],
-                            # partial captures model_succeeded[i] by value at loop time, not by reference
-                            is_connected=functools.partial(bool, model_succeeded[i]),
-                            db_session=db_session,
-                            assistant_message=setup.reserved_messages[i],
-                            llm=setup.llms[i],
-                            reserved_tokens=setup.reserved_token_count,
-                        )
-                    except Exception:
-                        logger.exception(
-                            f"Failed completion for model {i} on disconnect ({setup.model_display_names[i]})"
-                        )
-                yield Packet(
-                    placement=Placement(turn_index=last_turn_index + 1),
-                    obj=OverallStop(type="stop", stop_reason="user_cancelled"),
-                )
-                _completion_done = True
-                return
+                if not setup.check_is_connected():
+                    # Save state for every model before exiting.
+                    # - Succeeded models: full answer (is_connected=True).
+                    # - Still-in-flight models: partial answer + "stopped by user".
+                    # - Errored models: delete the orphaned reserved message; do NOT
+                    #   save "stopped by user" for a model that actually threw an exception.
+                    for i in range(n_models):
+                        if model_errored[i]:
+                            _delete_orphaned_message(i, "stop-button")
+                            continue
+                        try:
+                            succeeded = model_succeeded[i]
+                            llm_loop_completion_handle(
+                                state_container=state_containers[i],
+                                is_connected=lambda: succeeded,
+                                db_session=db_session,
+                                assistant_message=setup.reserved_messages[i],
+                                llm=setup.llms[i],
+                                reserved_tokens=setup.reserved_token_count,
+                            )
+                        except Exception:
+                            logger.exception(
+                                "stop-button completion failed for model %d (%s)",
+                                i,
+                                setup.model_display_names[i],
+                            )
+                    yield Packet(
+                        placement=Placement(turn_index=0),
+                        obj=OverallStop(type="stop", stop_reason="user_cancelled"),
+                    )
+                    completion_persisted = True
+                    return
+                continue
             else:
                 if item is _MODEL_DONE:
                     models_remaining -= 1
-                    continue
-
-                if isinstance(item, Exception):
+                elif isinstance(item, Exception):
                     # Yield a tagged error for this model but keep the other models running.
                     # Do NOT decrement models_remaining — _run_model's finally always posts
                     # _MODEL_DONE, which is the sole completion signal.
@@ -1157,14 +1200,7 @@ def _run_models(
                             "model_index": model_idx,
                         },
                     )
-                    continue
-
-                if isinstance(item, Packet):
-                    # Track the highest turn_index seen so OverallStop can follow it.
-                    if item.placement:
-                        last_turn_index = max(
-                            last_turn_index, item.placement.turn_index
-                        )
+                elif isinstance(item, Packet):
                     # model_index already embedded by the model's Emitter in _run_model
                     yield item
 
@@ -1174,6 +1210,8 @@ def _run_models(
         # sessions, but the main-thread db_session is unshared and safe to use.
         for i in range(n_models):
             if not model_succeeded[i]:
+                # Model errored — delete its orphaned reserved message.
+                _delete_orphaned_message(i, "normal")
                 continue
             try:
                 llm_loop_completion_handle(
@@ -1186,34 +1224,60 @@ def _run_models(
                 )
             except Exception:
                 logger.exception(
-                    f"Failed completion for model {i} ({setup.model_display_names[i]})"
+                    "normal completion failed for model %d (%s)",
+                    i,
+                    setup.model_display_names[i],
                 )
-        _completion_done = True
+        completion_persisted = True
 
     finally:
-        if _completion_done:
+        if completion_persisted:
             # Normal exit or stop-button exit: completion already persisted.
             # Threads are done (normal path) or can finish in the background (stop-button).
             executor.shutdown(wait=False)
         else:
             # Early exit (GeneratorExit from raw HTTP disconnect, or unhandled
             # exception in the drain loop).
-            # 1. Signal emitters to stop blocking — future emit() calls return immediately.
+            # 1. Signal emitters to stop — future emit() calls return immediately,
+            #    so workers exit their LLM loops promptly.
             drain_done.set()
-            # 2. Drain buffered packets from memory — no consumer is running.
+            # 2. Wait for all workers to finish. Once drain_done is set the Emitter
+            #    short-circuits, so workers should exit quickly.
+            executor.shutdown(wait=True)
+            # 3. All workers are done — complete from the main thread only.
+            for i in range(n_models):
+                if model_succeeded[i]:
+                    try:
+                        llm_loop_completion_handle(
+                            state_container=state_containers[i],
+                            # Model already finished — persist full response.
+                            is_connected=lambda: True,
+                            db_session=db_session,
+                            assistant_message=setup.reserved_messages[i],
+                            llm=setup.llms[i],
+                            reserved_tokens=setup.reserved_token_count,
+                        )
+                    except Exception:
+                        logger.exception(
+                            "disconnect completion failed for model %d (%s)",
+                            i,
+                            setup.model_display_names[i],
+                        )
+                elif model_errored[i]:
+                    _delete_orphaned_message(i, "disconnect")
+            # 4. Drain buffered packets from memory — no consumer is running.
             while not merged_queue.empty():
                 try:
                     merged_queue.get_nowait()
                 except queue.Empty:
                     break
-            # 3. Don't block the server thread — workers self-complete via drain_done.
-            executor.shutdown(wait=False)
 
 
-def handle_stream_message_objects(
+def _stream_chat_turn(
     new_msg_req: SendMessageRequest,
     user: User,
     db_session: Session,
+    llm_overrides: list[LLMOverride] | None = None,
     litellm_additional_headers: dict[str, str] | None = None,
     custom_tool_additional_headers: dict[str, str] | None = None,
     mcp_headers: dict[str, str] | None = None,
@@ -1222,17 +1286,23 @@ def handle_stream_message_objects(
     slack_context: SlackContext | None = None,
     external_state_container: ChatStateContainer | None = None,
 ) -> AnswerStream:
-    """Single-model streaming entrypoint.
+    """Private implementation for single-model and multi-model chat turn streaming.
 
     Builds the turn context via ``build_chat_turn``, then streams packets from
     ``_run_models`` back to the caller. Handles setup errors, LLM errors, and
     cancellation uniformly, saving whatever partial state has been accumulated
     before re-raising or yielding a terminal error packet.
 
+    Not called directly — use the public wrappers:
+    - ``handle_stream_message_objects`` for single-model (N=1) requests.
+    - ``handle_multi_model_stream`` for side-by-side multi-model comparison (N>1).
+
     Args:
         new_msg_req: The incoming chat request from the user.
         user: Authenticated user; may be anonymous for public personas.
         db_session: Database session for this request.
+        llm_overrides: ``None`` → single-model (persona default LLM).
+            Non-empty list → multi-model (one LLM per override, 2–3 items).
         litellm_additional_headers: Extra headers forwarded to the LLM provider.
         custom_tool_additional_headers: Extra headers for custom tool HTTP calls.
         mcp_headers: Extra headers for MCP tool calls.
@@ -1261,6 +1331,7 @@ def handle_stream_message_objects(
             new_msg_req=new_msg_req,
             user=user,
             db_session=db_session,
+            llm_overrides=llm_overrides,
             litellm_additional_headers=litellm_additional_headers,
             custom_tool_additional_headers=custom_tool_additional_headers,
             mcp_headers=mcp_headers,
@@ -1369,6 +1440,94 @@ def handle_stream_message_objects(
             logger.exception("Error in setting processing status")
 
 
+def handle_stream_message_objects(
+    new_msg_req: SendMessageRequest,
+    user: User,
+    db_session: Session,
+    litellm_additional_headers: dict[str, str] | None = None,
+    custom_tool_additional_headers: dict[str, str] | None = None,
+    mcp_headers: dict[str, str] | None = None,
+    bypass_acl: bool = False,
+    additional_context: str | None = None,
+    slack_context: SlackContext | None = None,
+    external_state_container: ChatStateContainer | None = None,
+) -> AnswerStream:
+    """Single-model streaming entrypoint. For multi-model comparison, use ``handle_multi_model_stream``."""
+    yield from _stream_chat_turn(
+        new_msg_req=new_msg_req,
+        user=user,
+        db_session=db_session,
+        llm_overrides=None,
+        litellm_additional_headers=litellm_additional_headers,
+        custom_tool_additional_headers=custom_tool_additional_headers,
+        mcp_headers=mcp_headers,
+        bypass_acl=bypass_acl,
+        additional_context=additional_context,
+        slack_context=slack_context,
+        external_state_container=external_state_container,
+    )
+
+
+def _build_model_display_name(override: LLMOverride | None) -> str:
+    """Build a human-readable display name from an LLM override."""
+    if override is None:
+        return "unknown"
+    return override.display_name or override.model_version or "unknown"
+
+
+def handle_multi_model_stream(
+    new_msg_req: SendMessageRequest,
+    user: User,
+    db_session: Session,
+    llm_overrides: list[LLMOverride],
+    litellm_additional_headers: dict[str, str] | None = None,
+    custom_tool_additional_headers: dict[str, str] | None = None,
+    mcp_headers: dict[str, str] | None = None,
+) -> AnswerStream:
+    """Thin wrapper for side-by-side multi-model comparison (2–3 models).
+
+    Validates the override list and delegates to ``_stream_chat_turn``,
+    which handles both single-model and multi-model execution via the same path.
+
+    Args:
+        new_msg_req: The incoming chat request. ``deep_research`` must be ``False``.
+        user: Authenticated user making the request.
+        db_session: Database session for this request.
+        llm_overrides: Exactly 2 or 3 ``LLMOverride`` objects — one per model to run.
+        litellm_additional_headers: Extra headers forwarded to each LLM provider.
+        custom_tool_additional_headers: Extra headers for custom tool HTTP calls.
+        mcp_headers: Extra headers for MCP tool calls.
+
+    Returns:
+        Generator yielding interleaved ``Packet`` objects from all models, each tagged
+        with ``model_index`` in its placement.
+    """
+    n_models = len(llm_overrides)
+    if n_models < 2 or n_models > 3:
+        yield StreamingError(
+            error=f"Multi-model requires 2-3 overrides, got {n_models}",
+            error_code="VALIDATION_ERROR",
+            is_retryable=False,
+        )
+        return
+    if new_msg_req.deep_research:
+        yield StreamingError(
+            error="Multi-model is not supported with deep research",
+            error_code="VALIDATION_ERROR",
+            is_retryable=False,
+        )
+        return
+    yield from _stream_chat_turn(
+        new_msg_req=new_msg_req,
+        user=user,
+        db_session=db_session,
+        llm_overrides=llm_overrides,
+        litellm_additional_headers=litellm_additional_headers,
+        custom_tool_additional_headers=custom_tool_additional_headers,
+        mcp_headers=mcp_headers,
+    )
+
+
 def llm_loop_completion_handle(
     state_container: ChatStateContainer,
     is_connected: Callable[[], bool],

backend/onyx/db/api_key.py

@@ -1,6 +1,7 @@
 import uuid
 
 from fastapi_users.password import PasswordHelper
+from sqlalchemy import delete
 from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession
 from sqlalchemy.orm import joinedload
@@ -10,14 +11,23 @@ from onyx.auth.api_key import ApiKeyDescriptor
 from onyx.auth.api_key import build_displayable_api_key
 from onyx.auth.api_key import generate_api_key
 from onyx.auth.api_key import hash_api_key
+from onyx.auth.schemas import UserRole
 from onyx.configs.constants import DANSWER_API_KEY_DUMMY_EMAIL_DOMAIN
 from onyx.configs.constants import DANSWER_API_KEY_PREFIX
 from onyx.configs.constants import UNNAMED_KEY_PLACEHOLDER
+from onyx.db.enums import AccountType
 from onyx.db.models import ApiKey
 from onyx.db.models import User
+from onyx.db.models import User__UserGroup
+from onyx.db.models import UserGroup
+from onyx.db.permissions import recompute_user_permissions__no_commit
+from onyx.db.users import assign_user_to_default_groups__no_commit
 from onyx.server.api_key.models import APIKeyArgs
+from onyx.utils.logger import setup_logger
 from shared_configs.contextvars import get_current_tenant_id
 
+logger = setup_logger()
+
 
 def get_api_key_email_pattern() -> str:
     return DANSWER_API_KEY_DUMMY_EMAIL_DOMAIN
@@ -85,6 +95,7 @@ def insert_api_key(
         is_superuser=False,
         is_verified=True,
         role=api_key_args.role,
+        account_type=AccountType.SERVICE_ACCOUNT,
     )
     db_session.add(api_key_user_row)
 
@@ -97,7 +108,18 @@ def insert_api_key(
     )
     db_session.add(api_key_row)
 
+    # Assign the API key virtual user to the appropriate default group
+    # before commit so everything is atomic.
+    # LIMITED role service accounts should have no group membership.
+    if api_key_args.role != UserRole.LIMITED:
+        assign_user_to_default_groups__no_commit(
+            db_session,
+            api_key_user_row,
+            is_admin=(api_key_args.role == UserRole.ADMIN),
+        )
+
     db_session.commit()
+
     return ApiKeyDescriptor(
         api_key_id=api_key_row.id,
         api_key_role=api_key_user_row.role,
@@ -124,7 +146,33 @@ def update_api_key(
 
     email_name = api_key_args.name or UNNAMED_KEY_PLACEHOLDER
     api_key_user.email = get_api_key_fake_email(email_name, str(api_key_user.id))
+
+    old_role = api_key_user.role
     api_key_user.role = api_key_args.role
+
+    # Reconcile default-group membership when the role changes.
+    if old_role != api_key_args.role:
+        # Remove from all default groups first.
+        delete_stmt = delete(User__UserGroup).where(
+            User__UserGroup.user_id == api_key_user.id,
+            User__UserGroup.user_group_id.in_(
+                select(UserGroup.id).where(UserGroup.is_default.is_(True))
+            ),
+        )
+        db_session.execute(delete_stmt)
+
+        # Re-assign to the correct default group (skip for LIMITED).
+        if api_key_args.role != UserRole.LIMITED:
+            assign_user_to_default_groups__no_commit(
+                db_session,
+                api_key_user,
+                is_admin=(api_key_args.role == UserRole.ADMIN),
+            )
+        else:
+            # No group assigned for LIMITED, but we still need to recompute
+            # since we just removed the old default-group membership above.
+            recompute_user_permissions__no_commit(api_key_user.id, db_session)
+
     db_session.commit()
 
     return ApiKeyDescriptor(

backend/onyx/db/chat.py

@@ -631,6 +631,91 @@ def reserve_message_id(
     return empty_message
 
 
+def reserve_multi_model_message_ids(
+    db_session: Session,
+    chat_session_id: UUID,
+    parent_message_id: int,
+    model_display_names: list[str],
+) -> list[ChatMessage]:
+    """Reserve N assistant message placeholders for multi-model parallel streaming.
+
+    All messages share the same parent (the user message). The parent's
+    latest_child_message_id points to the LAST reserved message so that the
+    default history-chain walker picks it up.
+    """
+    reserved: list[ChatMessage] = []
+    for display_name in model_display_names:
+        msg = ChatMessage(
+            chat_session_id=chat_session_id,
+            parent_message_id=parent_message_id,
+            latest_child_message_id=None,
+            message="Response was terminated prior to completion, try regenerating.",
+            token_count=15,  # placeholder; updated on completion by llm_loop_completion_handle
+            message_type=MessageType.ASSISTANT,
+            model_display_name=display_name,
+        )
+        db_session.add(msg)
+        reserved.append(msg)
+
+    # Flush to assign IDs without committing yet
+    db_session.flush()
+
+    # Point parent's latest_child to the last reserved message
+    parent = (
+        db_session.query(ChatMessage)
+        .filter(ChatMessage.id == parent_message_id)
+        .first()
+    )
+    if parent:
+        parent.latest_child_message_id = reserved[-1].id
+
+    db_session.commit()
+    return reserved
+
+
+def set_preferred_response(
+    db_session: Session,
+    user_message_id: int,
+    preferred_assistant_message_id: int,
+) -> None:
+    """Mark one assistant response as the user's preferred choice in a multi-model turn.
+
+    Also advances ``latest_child_message_id`` so the preferred response becomes
+    the active branch for any subsequent messages in the conversation.
+
+    Args:
+        db_session: Active database session.
+        user_message_id: Primary key of the ``USER``-type ``ChatMessage`` whose
+            preferred response is being set.
+        preferred_assistant_message_id: Primary key of the ``ASSISTANT``-type
+            ``ChatMessage`` to prefer. Must be a direct child of ``user_message_id``.
+
+    Raises:
+        ValueError: If either message is not found, if ``user_message_id`` does not
+            refer to a USER message, or if the assistant message is not a direct child
+            of the user message.
+    """
+    user_msg = db_session.get(ChatMessage, user_message_id)
+    if user_msg is None:
+        raise ValueError(f"User message {user_message_id} not found")
+    if user_msg.message_type != MessageType.USER:
+        raise ValueError(f"Message {user_message_id} is not a user message")
+
+    assistant_msg = db_session.get(ChatMessage, preferred_assistant_message_id)
+    if assistant_msg is None:
+        raise ValueError(
+            f"Assistant message {preferred_assistant_message_id} not found"
+        )
+    if assistant_msg.parent_message_id != user_message_id:
+        raise ValueError(
+            f"Assistant message {preferred_assistant_message_id} is not a child of user message {user_message_id}"
+        )
+
+    user_msg.preferred_response_id = preferred_assistant_message_id
+    user_msg.latest_child_message_id = preferred_assistant_message_id
+    db_session.commit()
+
+
 def create_new_chat_message(
     chat_session_id: UUID,
     parent_message: ChatMessage,
@@ -853,6 +938,8 @@ def translate_db_message_to_chat_message_detail(
         error=chat_message.error,
         current_feedback=current_feedback,
         processing_duration_seconds=chat_message.processing_duration_seconds,
+        preferred_response_id=chat_message.preferred_response_id,
+        model_display_name=chat_message.model_display_name,
     )
 
     return chat_msg_detail

backend/onyx/db/enums.py

@@ -13,19 +13,26 @@ class AccountType(str, PyEnum):
     BOT, EXT_PERM_USER, ANONYMOUS → fixed behavior
     """
 
-    STANDARD = "standard"
-    BOT = "bot"
-    EXT_PERM_USER = "ext_perm_user"
-    SERVICE_ACCOUNT = "service_account"
-    ANONYMOUS = "anonymous"
+    STANDARD = "STANDARD"
+    BOT = "BOT"
+    EXT_PERM_USER = "EXT_PERM_USER"
+    SERVICE_ACCOUNT = "SERVICE_ACCOUNT"
+    ANONYMOUS = "ANONYMOUS"
+
+    def is_web_login(self) -> bool:
+        """Whether this account type supports interactive web login."""
+        return self not in (
+            AccountType.BOT,
+            AccountType.EXT_PERM_USER,
+        )
 
 
 class GrantSource(str, PyEnum):
     """How a permission grant was created."""
 
-    USER = "user"
-    SCIM = "scim"
-    SYSTEM = "system"
+    USER = "USER"
+    SCIM = "SCIM"
+    SYSTEM = "SYSTEM"
 
 
 class IndexingStatus(str, PyEnum):

backend/onyx/db/models.py

@@ -305,8 +305,11 @@ class User(SQLAlchemyBaseUserTableUUID, Base):
     role: Mapped[UserRole] = mapped_column(
         Enum(UserRole, native_enum=False, default=UserRole.BASIC)
     )
-    account_type: Mapped[AccountType | None] = mapped_column(
-        Enum(AccountType, native_enum=False), nullable=True
+    account_type: Mapped[AccountType] = mapped_column(
+        Enum(AccountType, native_enum=False),
+        nullable=False,
+        default=AccountType.STANDARD,
+        server_default="STANDARD",
     )
 
     """
@@ -353,6 +356,13 @@ class User(SQLAlchemyBaseUserTableUUID, Base):
         postgresql.JSONB(), nullable=True, default=None
     )
 
+    effective_permissions: Mapped[list[str]] = mapped_column(
+        postgresql.JSONB(),
+        nullable=False,
+        default=list,
+        server_default=text("'[]'::jsonb"),
+    )
+
     oidc_expiry: Mapped[datetime.datetime] = mapped_column(
         TIMESTAMPAware(timezone=True), nullable=True
     )
@@ -4016,7 +4026,12 @@ class PermissionGrant(Base):
         ForeignKey("user_group.id", ondelete="CASCADE"), nullable=False
     )
     permission: Mapped[Permission] = mapped_column(
-        Enum(Permission, native_enum=False), nullable=False
+        Enum(
+            Permission,
+            native_enum=False,
+            values_callable=lambda x: [e.value for e in x],
+        ),
+        nullable=False,
     )
     grant_source: Mapped[GrantSource] = mapped_column(
         Enum(GrantSource, native_enum=False), nullable=False

backend/onyx/db/permissions.py

@@ -0,0 +1,95 @@
+"""
+DB operations for recomputing user effective_permissions.
+
+These live in onyx/db/ (not onyx/auth/) because they are pure DB operations
+that query PermissionGrant rows and update the User.effective_permissions
+JSONB column.  Keeping them here avoids circular imports when called from
+other onyx/db/ modules such as users.py.
+"""
+
+from collections import defaultdict
+from uuid import UUID
+
+from sqlalchemy import select
+from sqlalchemy import update
+from sqlalchemy.orm import Session
+
+from onyx.db.models import PermissionGrant
+from onyx.db.models import User
+from onyx.db.models import User__UserGroup
+
+
+def recompute_user_permissions__no_commit(
+    user_ids: UUID | str | list[UUID] | list[str], db_session: Session
+) -> None:
+    """Recompute granted permissions for one or more users.
+
+    Accepts a single UUID or a list.  Uses a single query regardless of
+    how many users are passed, avoiding N+1 issues.
+
+    Stores only directly granted permissions — implication expansion
+    happens at read time via get_effective_permissions().
+
+    Does NOT commit — caller must commit the session.
+    """
+    if isinstance(user_ids, (UUID, str)):
+        uid_list = [user_ids]
+    else:
+        uid_list = list(user_ids)
+
+    if not uid_list:
+        return
+
+    # Single query to fetch ALL permissions for these users across ALL their
+    # groups (a user may belong to multiple groups with different grants).
+    rows = db_session.execute(
+        select(User__UserGroup.user_id, PermissionGrant.permission)
+        .join(
+            PermissionGrant,
+            PermissionGrant.group_id == User__UserGroup.user_group_id,
+        )
+        .where(
+            User__UserGroup.user_id.in_(uid_list),
+            PermissionGrant.is_deleted.is_(False),
+        )
+    ).all()
+
+    # Group permissions by user; users with no grants get an empty set.
+    perms_by_user: dict[UUID | str, set[str]] = defaultdict(set)
+    for uid in uid_list:
+        perms_by_user[uid]  # ensure every user has an entry
+    for uid, perm in rows:
+        perms_by_user[uid].add(perm.value)
+
+    for uid, perms in perms_by_user.items():
+        db_session.execute(
+            update(User)
+            .where(User.id == uid)  # type: ignore[arg-type]
+            .values(effective_permissions=sorted(perms))
+        )
+
+
+def recompute_permissions_for_group__no_commit(
+    group_id: int, db_session: Session
+) -> None:
+    """Recompute granted permissions for all users in a group.
+
+    Does NOT commit — caller must commit the session.
+    """
+    user_ids: list[UUID] = [
+        uid
+        for uid in db_session.execute(
+            select(User__UserGroup.user_id).where(
+                User__UserGroup.user_group_id == group_id,
+                User__UserGroup.user_id.isnot(None),
+            )
+        )
+        .scalars()
+        .all()
+        if uid is not None
+    ]
+
+    if not user_ids:
+        return
+
+    recompute_user_permissions__no_commit(user_ids, db_session)

backend/onyx/db/release_notes.py

@@ -5,11 +5,11 @@ from urllib.parse import urlencode
 from sqlalchemy import select
 from sqlalchemy.orm import Session
 
-from onyx.auth.schemas import UserRole
 from onyx.configs.app_configs import INSTANCE_TYPE
 from onyx.configs.constants import DANSWER_API_KEY_DUMMY_EMAIL_DOMAIN
 from onyx.configs.constants import NotificationType
 from onyx.configs.constants import ONYX_UTM_SOURCE
+from onyx.db.enums import AccountType
 from onyx.db.models import User
 from onyx.db.notification import batch_create_notifications
 from onyx.server.features.release_notes.constants import DOCS_CHANGELOG_BASE_URL
@@ -49,7 +49,7 @@ def create_release_notifications_for_versions(
         db_session.scalars(
             select(User.id).where(  # type: ignore
                 User.is_active == True,  # noqa: E712
-                User.role.notin_([UserRole.SLACK_USER, UserRole.EXT_PERM_USER]),
+                User.account_type.notin_([AccountType.BOT, AccountType.EXT_PERM_USER]),
                 User.email.endswith(DANSWER_API_KEY_DUMMY_EMAIL_DOMAIN).is_(False),  # type: ignore[attr-defined]
             )
         ).all()

backend/onyx/db/user_preferences.py

@@ -9,12 +9,17 @@ from sqlalchemy import update
 from sqlalchemy.orm import Session
 
 from onyx.auth.schemas import UserRole
+from onyx.db.enums import AccountType
 from onyx.db.enums import DefaultAppMode
 from onyx.db.enums import ThemePreference
 from onyx.db.models import AccessToken
 from onyx.db.models import Assistant__UserSpecificConfig
 from onyx.db.models import Memory
 from onyx.db.models import User
+from onyx.db.models import User__UserGroup
+from onyx.db.models import UserGroup
+from onyx.db.permissions import recompute_user_permissions__no_commit
+from onyx.db.users import assign_user_to_default_groups__no_commit
 from onyx.server.manage.models import MemoryItem
 from onyx.server.manage.models import UserSpecificAssistantPreference
 from onyx.utils.logger import setup_logger
@@ -23,13 +28,53 @@ from onyx.utils.logger import setup_logger
 logger = setup_logger()
 
 
+_ROLE_TO_ACCOUNT_TYPE: dict[UserRole, AccountType] = {
+    UserRole.SLACK_USER: AccountType.BOT,
+    UserRole.EXT_PERM_USER: AccountType.EXT_PERM_USER,
+}
+
+
 def update_user_role(
     user: User,
     new_role: UserRole,
     db_session: Session,
 ) -> None:
-    """Update a user's role in the database."""
+    """Update a user's role in the database.
+    Dual-writes account_type to keep it in sync with role and
+    reconciles default-group membership (Admin / Basic)."""
+    old_role = user.role
     user.role = new_role
+    # Note: setting account_type to BOT or EXT_PERM_USER causes
+    # assign_user_to_default_groups__no_commit to early-return, which is
+    # intentional — these account types should not be in default groups.
+    if new_role in _ROLE_TO_ACCOUNT_TYPE:
+        user.account_type = _ROLE_TO_ACCOUNT_TYPE[new_role]
+    elif user.account_type in (AccountType.BOT, AccountType.EXT_PERM_USER):
+        # Upgrading from a non-web-login account type to a web role
+        user.account_type = AccountType.STANDARD
+
+    # Reconcile default-group membership when the role changes.
+    if old_role != new_role:
+        # Remove from all default groups first.
+        db_session.execute(
+            delete(User__UserGroup).where(
+                User__UserGroup.user_id == user.id,
+                User__UserGroup.user_group_id.in_(
+                    select(UserGroup.id).where(UserGroup.is_default.is_(True))
+                ),
+            )
+        )
+
+        # Re-assign to the correct default group (skip for LIMITED).
+        if new_role != UserRole.LIMITED:
+            assign_user_to_default_groups__no_commit(
+                db_session,
+                user,
+                is_admin=(new_role == UserRole.ADMIN),
+            )
+
+        recompute_user_permissions__no_commit(user.id, db_session)
+
     db_session.commit()
 
 
@@ -47,8 +92,16 @@ def activate_user(
     user: User,
     db_session: Session,
 ) -> None:
-    """Activate a user by setting is_active to True."""
+    """Activate a user by setting is_active to True.
+
+    Also reconciles default-group membership — the user may have been
+    created while inactive or deactivated before the backfill migration.
+    """
     user.is_active = True
+    if user.role != UserRole.LIMITED:
+        assign_user_to_default_groups__no_commit(
+            db_session, user, is_admin=(user.role == UserRole.ADMIN)
+        )
     db_session.add(user)
     db_session.commit()
 

backend/onyx/db/users.py

@@ -17,8 +17,9 @@ from sqlalchemy.sql.expression import or_
 from onyx.auth.invited_users import remove_user_from_invited_users
 from onyx.auth.schemas import UserRole
 from onyx.configs.constants import ANONYMOUS_USER_EMAIL
+from onyx.configs.constants import DANSWER_API_KEY_DUMMY_EMAIL_DOMAIN
 from onyx.configs.constants import NO_AUTH_PLACEHOLDER_USER_EMAIL
-from onyx.db.api_key import DANSWER_API_KEY_DUMMY_EMAIL_DOMAIN
+from onyx.db.enums import AccountType
 from onyx.db.models import DocumentSet
 from onyx.db.models import DocumentSet__User
 from onyx.db.models import Persona
@@ -27,11 +28,17 @@ from onyx.db.models import SamlAccount
 from onyx.db.models import User
 from onyx.db.models import User__UserGroup
 from onyx.db.models import UserGroup
+from onyx.utils.logger import setup_logger
 from onyx.utils.variable_functionality import fetch_ee_implementation_or_noop
 
+logger = setup_logger()
+
 
 def validate_user_role_update(
-    requested_role: UserRole, current_role: UserRole, explicit_override: bool = False
+    requested_role: UserRole,
+    current_role: UserRole,
+    current_account_type: AccountType,
+    explicit_override: bool = False,
 ) -> None:
     """
     Validate that a user role update is valid.
@@ -41,19 +48,18 @@ def validate_user_role_update(
     - requested role is a slack user
     - requested role is an external permissioned user
     - requested role is a limited user
-    - current role is a slack user
-    - current role is an external permissioned user
+    - current account type is BOT (slack user)
+    - current account type is EXT_PERM_USER
     - current role is a limited user
     """
 
-    if current_role == UserRole.SLACK_USER:
+    if current_account_type == AccountType.BOT:
         raise HTTPException(
             status_code=400,
             detail="To change a Slack User's role, they must first login to Onyx via the web app.",
         )
 
-    if current_role == UserRole.EXT_PERM_USER:
-        # This shouldn't happen, but just in case
+    if current_account_type == AccountType.EXT_PERM_USER:
         raise HTTPException(
             status_code=400,
             detail="To change an External Permissioned User's role, they must first login to Onyx via the web app.",
@@ -298,6 +304,7 @@ def _generate_slack_user(email: str) -> User:
         email=email,
         hashed_password=hashed_pass,
         role=UserRole.SLACK_USER,
+        account_type=AccountType.BOT,
     )
 
 
@@ -306,8 +313,9 @@ def add_slack_user_if_not_exists(db_session: Session, email: str) -> User:
     user = get_user_by_email(email, db_session)
     if user is not None:
         # If the user is an external permissioned user, we update it to a slack user
-        if user.role == UserRole.EXT_PERM_USER:
+        if user.account_type == AccountType.EXT_PERM_USER:
             user.role = UserRole.SLACK_USER
+            user.account_type = AccountType.BOT
             db_session.commit()
         return user
 
@@ -344,6 +352,7 @@ def _generate_ext_permissioned_user(email: str) -> User:
         email=email,
         hashed_password=hashed_pass,
         role=UserRole.EXT_PERM_USER,
+        account_type=AccountType.EXT_PERM_USER,
     )
 
 
@@ -375,6 +384,81 @@ def batch_add_ext_perm_user_if_not_exists(
     return all_users
 
 
+def assign_user_to_default_groups__no_commit(
+    db_session: Session,
+    user: User,
+    is_admin: bool = False,
+) -> None:
+    """Assign a newly created user to the appropriate default group.
+
+    Does NOT commit — callers must commit the session themselves so that
+    group assignment can be part of the same transaction as user creation.
+
+    Args:
+        is_admin: If True, assign to Admin default group; otherwise Basic.
+            Callers determine this from their own context (e.g. user_count,
+            admin email list, explicit choice). Defaults to False (Basic).
+    """
+    if user.account_type in (
+        AccountType.BOT,
+        AccountType.EXT_PERM_USER,
+        AccountType.ANONYMOUS,
+    ):
+        return
+
+    target_group_name = "Admin" if is_admin else "Basic"
+
+    default_group = (
+        db_session.query(UserGroup)
+        .filter(
+            UserGroup.name == target_group_name,
+            UserGroup.is_default.is_(True),
+        )
+        .first()
+    )
+
+    if default_group is None:
+        raise RuntimeError(
+            f"Default group '{target_group_name}' not found. "
+            f"Cannot assign user {user.email} to a group. "
+            f"Ensure the seed_default_groups migration has run."
+        )
+
+    # Check if the user is already in the group
+    existing = (
+        db_session.query(User__UserGroup)
+        .filter(
+            User__UserGroup.user_id == user.id,
+            User__UserGroup.user_group_id == default_group.id,
+        )
+        .first()
+    )
+    if existing is not None:
+        return
+
+    savepoint = db_session.begin_nested()
+    try:
+        db_session.add(
+            User__UserGroup(
+                user_id=user.id,
+                user_group_id=default_group.id,
+            )
+        )
+        db_session.flush()
+    except IntegrityError:
+        # Race condition: another transaction inserted this membership
+        # between our SELECT and INSERT. The savepoint isolates the failure
+        # so the outer transaction (user creation) stays intact.
+        savepoint.rollback()
+        return
+
+    from onyx.db.permissions import recompute_user_permissions__no_commit
+
+    recompute_user_permissions__no_commit(user.id, db_session)
+
+    logger.info(f"Assigned user {user.email} to default group '{default_group.name}'")
+
+
 def delete_user_from_db(
     user_to_delete: User,
     db_session: Session,
@@ -421,13 +505,14 @@ def delete_user_from_db(
 def batch_get_user_groups(
     db_session: Session,
     user_ids: list[UUID],
+    include_default: bool = False,
 ) -> dict[UUID, list[tuple[int, str]]]:
     """Fetch group memberships for a batch of users in a single query.
     Returns a mapping of user_id -> list of (group_id, group_name) tuples."""
     if not user_ids:
         return {}
 
-    rows = db_session.execute(
+    stmt = (
         select(
             User__UserGroup.user_id,
             UserGroup.id,
@@ -435,7 +520,11 @@ def batch_get_user_groups(
         )
         .join(UserGroup, UserGroup.id == User__UserGroup.user_group_id)
         .where(User__UserGroup.user_id.in_(user_ids))
-    ).all()
+    )
+    if not include_default:
+        stmt = stmt.where(UserGroup.is_default == False)  # noqa: E712
+
+    rows = db_session.execute(stmt).all()
 
     result: dict[UUID, list[tuple[int, str]]] = {uid: [] for uid in user_ids}
     for user_id, group_id, group_name in rows:

backend/onyx/onyxbot/slack/handlers/handle_message.py

@@ -3,10 +3,10 @@ import datetime
 from slack_sdk import WebClient
 from slack_sdk.errors import SlackApiError
 
-from onyx.auth.schemas import UserRole
 from onyx.configs.onyxbot_configs import ONYX_BOT_FEEDBACK_REMINDER
 from onyx.configs.onyxbot_configs import ONYX_BOT_REACT_EMOJI
 from onyx.db.engine.sql_engine import get_session_with_current_tenant
+from onyx.db.enums import AccountType
 from onyx.db.models import SlackChannelConfig
 from onyx.db.user_preferences import activate_user
 from onyx.db.users import add_slack_user_if_not_exists
@@ -247,7 +247,7 @@ def handle_message(
 
             elif (
                 not existing_user.is_active
-                and existing_user.role == UserRole.SLACK_USER
+                and existing_user.account_type == AccountType.BOT
             ):
                 check_seat_fn = fetch_ee_implementation_or_noop(
                     "onyx.db.license",

backend/onyx/server/documents/cc_pair.py

@@ -59,9 +59,6 @@ from onyx.db.permission_sync_attempt import (
 from onyx.redis.redis_connector import RedisConnector
 from onyx.redis.redis_connector_utils import get_deletion_attempt_snapshot
 from onyx.redis.redis_pool import get_redis_client
-from onyx.server.documents.mock_connector_data import get_mock_cc_pair_full_info
-from onyx.server.documents.mock_connector_data import get_mock_index_attempts
-from onyx.server.documents.mock_connector_data import load_mock_data
 from onyx.server.documents.models import CCPairFullInfo
 from onyx.server.documents.models import CCPropertyUpdateRequest
 from onyx.server.documents.models import CCStatusUpdateRequest
@@ -88,18 +85,6 @@ def get_cc_pair_index_attempts(
     user: User = Depends(current_curator_or_admin_user),
     db_session: Session = Depends(get_session),
 ) -> PaginatedReturn[IndexAttemptSnapshot]:
-    mock_data = load_mock_data()
-    if mock_data is not None:
-        mock_attempts = get_mock_index_attempts(mock_data, cc_pair_id)
-        if mock_attempts is not None:
-            all_items = [IndexAttemptSnapshot(**a) for a in mock_attempts]
-            start = page_num * page_size
-            page_items = all_items[start : start + page_size]
-            return PaginatedReturn(
-                items=page_items,
-                total_items=len(all_items),
-            )
-
     if user:
         user_has_access = verify_user_has_access_to_cc_pair(
             cc_pair_id, db_session, user, get_editable=False
@@ -172,12 +157,6 @@ def get_cc_pair_full_info(
     user: User = Depends(current_curator_or_admin_user),
     db_session: Session = Depends(get_session),
 ) -> CCPairFullInfo:
-    mock_data = load_mock_data()
-    if mock_data is not None:
-        mock_info = get_mock_cc_pair_full_info(mock_data, cc_pair_id)
-        if mock_info is not None:
-            return CCPairFullInfo(**mock_info)
-
     tenant_id = get_current_tenant_id()
 
     cc_pair = get_connector_credential_pair_from_id_for_user(

backend/onyx/server/documents/connector.py

@@ -32,6 +32,7 @@ from onyx.background.celery.tasks.pruning.tasks import (
 from onyx.background.celery.versioned_apps.client import app as client_app
 from onyx.configs.app_configs import EMAIL_CONFIGURED
 from onyx.configs.app_configs import ENABLED_CONNECTOR_TYPES
+from onyx.configs.app_configs import MOCK_CONNECTOR_FILE_PATH
 from onyx.configs.constants import DocumentSource
 from onyx.configs.constants import FileOrigin
 from onyx.configs.constants import MilestoneRecordType
@@ -124,8 +125,6 @@ from onyx.file_store.file_store import FileStore
 from onyx.file_store.file_store import get_default_file_store
 from onyx.key_value_store.interface import KvKeyNotFoundError
 from onyx.redis.redis_pool import get_redis_client
-from onyx.server.documents.mock_connector_data import get_mock_indexing_statuses
-from onyx.server.documents.mock_connector_data import load_mock_data
 from onyx.server.documents.models import AuthStatus
 from onyx.server.documents.models import AuthUrl
 from onyx.server.documents.models import ConnectorBase
@@ -1116,27 +1115,28 @@ def get_connector_indexing_status(
     # sqlalchemy-method-connection-for-bind-is-already-in-progress
     # for why we can't pass in the current db_session to these functions
 
-    mock_data = load_mock_data()
-    if mock_data is not None:
-        mock_statuses = get_mock_indexing_statuses(mock_data)
-        if mock_statuses is not None:
+    if MOCK_CONNECTOR_FILE_PATH:
+        import json
+
+        with open(MOCK_CONNECTOR_FILE_PATH, "r") as f:
+            raw_data = json.load(f)
             connector_indexing_statuses = [
-                ConnectorIndexingStatusLite(**status) for status in mock_statuses
-            ]
-            return [
-                ConnectorIndexingStatusLiteResponse(
-                    source=DocumentSource.FILE,
-                    summary=SourceSummary(
-                        total_connectors=100,
-                        active_connectors=100,
-                        public_connectors=100,
-                        total_docs_indexed=100000,
-                    ),
-                    current_page=1,
-                    total_pages=1,
-                    indexing_statuses=connector_indexing_statuses,
-                )
+                ConnectorIndexingStatusLite(**status) for status in raw_data
             ]
+        return [
+            ConnectorIndexingStatusLiteResponse(
+                source=DocumentSource.FILE,
+                summary=SourceSummary(
+                    total_connectors=100,
+                    active_connectors=100,
+                    public_connectors=100,
+                    total_docs_indexed=100000,
+                ),
+                current_page=1,
+                total_pages=1,
+                indexing_statuses=connector_indexing_statuses,
+            )
+        ]
 
     parallel_functions: list[tuple[CallableProtocol, tuple[Any, ...]]] = [
         # Get editable connector/credential pairs

backend/onyx/server/documents/mock_connector_data.py

@@ -1,133 +0,0 @@
-"""Utilities for loading mock connector data from a JSON file.
-
-When MOCK_CONNECTOR_FILE_PATH is set, the backend serves connector listing,
-detail, and index-attempt endpoints from a static JSON file instead of hitting
-the database.  This is useful for frontend development and demos.
-
-Time-offset support
--------------------
-Any datetime string field in the JSON can be replaced with an *offset string*
-of the form ``"<offset_seconds>"``, e.g. ``"-3600"`` means "1 hour ago" and
-``"-86400"`` means "24 hours ago".  Positive values point to the future.
-The offset is resolved to an absolute ISO-8601 datetime at load time, so
-each request gets a fresh "now".
-"""
-
-import json
-from datetime import datetime
-from datetime import timedelta
-from datetime import timezone
-from typing import Any
-
-from onyx.configs.app_configs import MOCK_CONNECTOR_FILE_PATH
-from onyx.utils.logger import setup_logger
-
-logger = setup_logger()
-
-# ---- JSON schema top-level keys ------------------------------------------------
-_KEY_INDEXING_STATUSES = "indexing_statuses"
-_KEY_CC_PAIR_FULL_INFO = "cc_pair_full_info"
-_KEY_INDEX_ATTEMPTS = "index_attempts"
-
-# Fields across the relevant Pydantic models that hold datetimes.
-_DATETIME_FIELDS: set[str] = {
-    # ConnectorIndexingStatusLite
-    "last_success",
-    # CCPairFullInfo
-    "last_indexed",
-    "last_pruned",
-    "last_full_permission_sync",
-    "last_permission_sync_attempt_finished",
-    # ConnectorSnapshot / CredentialSnapshot
-    "time_created",
-    "time_updated",
-    "indexing_start",
-    # IndexAttemptSnapshot
-    "time_started",
-    "time_updated",
-    "poll_range_start",
-    "poll_range_end",
-    # IndexAttemptErrorPydantic
-    "failed_time_range_start",
-    "failed_time_range_end",
-    "time_created",
-}
-
-
-def _resolve_time_offsets(obj: Any) -> Any:
-    """Walk a JSON-like structure and resolve offset strings to ISO datetimes.
-
-    An offset string is a string that, after stripping whitespace, is parseable
-    as an integer or float.  It represents seconds relative to *now*.
-    """
-    now = datetime.now(tz=timezone.utc)
-
-    if isinstance(obj, dict):
-        return {k: _resolve_value(k, v, now) for k, v in obj.items()}
-    if isinstance(obj, list):
-        return [_resolve_time_offsets(item) for item in obj]
-    return obj
-
-
-def _resolve_value(key: str, value: Any, now: datetime) -> Any:
-    if isinstance(value, dict):
-        return {k: _resolve_value(k, v, now) for k, v in value.items()}
-    if isinstance(value, list):
-        return [_resolve_time_offsets(item) for item in value]
-    if key in _DATETIME_FIELDS and isinstance(value, str):
-        try:
-            offset_seconds = float(value)
-            return (now + timedelta(seconds=offset_seconds)).isoformat()
-        except ValueError:
-            # Not a numeric string – leave it as-is (already an ISO datetime).
-            pass
-    return value
-
-
-def _load_raw() -> dict[str, Any] | None:
-    """Load and return the raw JSON from MOCK_CONNECTOR_FILE_PATH, or None."""
-    if not MOCK_CONNECTOR_FILE_PATH:
-        return None
-    with open(MOCK_CONNECTOR_FILE_PATH) as f:
-        return json.load(f)  # type: ignore[no-any-return]
-
-
-def load_mock_data() -> dict[str, Any] | None:
-    """Load mock data with time offsets resolved. Returns None when mocking is
-    disabled."""
-    raw = _load_raw()
-    if raw is None:
-        return None
-
-    # Support both the old format (bare list of indexing statuses) and the new
-    # format (dict with explicit keys).
-    if isinstance(raw, list):
-        raw = {_KEY_INDEXING_STATUSES: raw}
-
-    return _resolve_time_offsets(raw)  # type: ignore[return-value]
-
-
-def get_mock_indexing_statuses(
-    data: dict[str, Any],
-) -> list[dict[str, Any]] | None:
-    return data.get(_KEY_INDEXING_STATUSES)
-
-
-def get_mock_cc_pair_full_info(
-    data: dict[str, Any],
-    cc_pair_id: int,
-) -> dict[str, Any] | None:
-    by_id = data.get(_KEY_CC_PAIR_FULL_INFO)
-    if not by_id:
-        return None
-    return by_id.get(str(cc_pair_id))
-
-
-def get_mock_index_attempts(
-    data: dict[str, Any],
-    cc_pair_id: int,
-) -> list[dict[str, Any]] | None:
-    by_id = data.get(_KEY_INDEX_ATTEMPTS)
-    if not by_id:
-        return None
-    return by_id.get(str(cc_pair_id))

backend/onyx/server/manage/users.py

@@ -27,6 +27,7 @@ from onyx.auth.email_utils import send_user_email_invite
 from onyx.auth.invited_users import get_invited_users
 from onyx.auth.invited_users import remove_user_from_invited_users
 from onyx.auth.invited_users import write_invited_users
+from onyx.auth.permissions import get_effective_permissions
 from onyx.auth.schemas import UserRole
 from onyx.auth.users import anonymous_user_enabled
 from onyx.auth.users import current_admin_user
@@ -50,6 +51,7 @@ from onyx.configs.constants import PUBLIC_API_TAGS
 from onyx.db.api_key import is_api_key_email_address
 from onyx.db.auth import get_live_users_count
 from onyx.db.engine.sql_engine import get_session
+from onyx.db.enums import AccountType
 from onyx.db.enums import UserFileStatus
 from onyx.db.models import User
 from onyx.db.models import UserFile
@@ -142,6 +144,7 @@ def set_user_role(
     validate_user_role_update(
         requested_role=requested_role,
         current_role=current_role,
+        current_account_type=user_to_update.account_type,
         explicit_override=user_role_update_request.explicit_override,
     )
 
@@ -327,8 +330,8 @@ def list_all_users(
         if (include_api_keys or not is_api_key_email_address(user.email))
     ]
 
-    slack_users = [user for user in users if user.role == UserRole.SLACK_USER]
-    accepted_users = [user for user in users if user.role != UserRole.SLACK_USER]
+    slack_users = [user for user in users if user.account_type == AccountType.BOT]
+    accepted_users = [user for user in users if user.account_type != AccountType.BOT]
 
     accepted_emails = {user.email for user in accepted_users}
     slack_users_emails = {user.email for user in slack_users}
@@ -671,7 +674,7 @@ def list_all_users_basic_info(
     return [
         MinimalUserSnapshot(id=user.id, email=user.email)
         for user in users
-        if user.role != UserRole.SLACK_USER
+        if user.account_type != AccountType.BOT
         and (include_api_keys or not is_api_key_email_address(user.email))
     ]
 
@@ -774,6 +777,13 @@ def _get_token_created_at(
     return get_current_token_creation_postgres(user, db_session)
 
 
+@router.get("/me/permissions", tags=PUBLIC_API_TAGS)
+def get_current_user_permissions(
+    user: User = Depends(current_user),
+) -> list[str]:
+    return sorted(p.value for p in get_effective_permissions(user))
+
+
 @router.get("/me", tags=PUBLIC_API_TAGS)
 def verify_user_logged_in(
     request: Request,

backend/onyx/server/models.py

@@ -7,6 +7,7 @@ from uuid import UUID
 from pydantic import BaseModel
 
 from onyx.auth.schemas import UserRole
+from onyx.db.enums import AccountType
 from onyx.db.models import User
 
 
@@ -41,6 +42,7 @@ class FullUserSnapshot(BaseModel):
     id: UUID
     email: str
     role: UserRole
+    account_type: AccountType
     is_active: bool
     password_configured: bool
     personal_name: str | None
@@ -60,6 +62,7 @@ class FullUserSnapshot(BaseModel):
             id=user.id,
             email=user.email,
             role=user.role,
+            account_type=user.account_type,
             is_active=user.is_active,
             password_configured=user.password_configured,
             personal_name=user.personal_name,

backend/onyx/server/query_and_chat/chat_backend.py

@@ -28,6 +28,7 @@ from onyx.chat.chat_utils import extract_headers
 from onyx.chat.models import ChatFullResponse
 from onyx.chat.models import CreateChatSessionID
 from onyx.chat.process_message import gather_stream_full
+from onyx.chat.process_message import handle_multi_model_stream
 from onyx.chat.process_message import handle_stream_message_objects
 from onyx.chat.prompt_utils import get_default_base_system_prompt
 from onyx.chat.stop_signal_checker import set_fence
@@ -46,6 +47,7 @@ from onyx.db.chat import get_chat_messages_by_session
 from onyx.db.chat import get_chat_session_by_id
 from onyx.db.chat import get_chat_sessions_by_user
 from onyx.db.chat import set_as_latest_chat_message
+from onyx.db.chat import set_preferred_response
 from onyx.db.chat import translate_db_message_to_chat_message_detail
 from onyx.db.chat import update_chat_session
 from onyx.db.chat_search import search_chat_sessions
@@ -60,6 +62,8 @@ from onyx.db.persona import get_persona_by_id
 from onyx.db.usage import increment_usage
 from onyx.db.usage import UsageType
 from onyx.db.user_file import get_file_id_by_user_file_id
+from onyx.error_handling.error_codes import OnyxErrorCode
+from onyx.error_handling.exceptions import OnyxError
 from onyx.file_store.file_store import get_default_file_store
 from onyx.llm.constants import LlmProviderNames
 from onyx.llm.factory import get_default_llm
@@ -81,6 +85,7 @@ from onyx.server.query_and_chat.models import ChatSessionUpdateRequest
 from onyx.server.query_and_chat.models import MessageOrigin
 from onyx.server.query_and_chat.models import RenameChatSessionResponse
 from onyx.server.query_and_chat.models import SendMessageRequest
+from onyx.server.query_and_chat.models import SetPreferredResponseRequest
 from onyx.server.query_and_chat.models import UpdateChatSessionTemperatureRequest
 from onyx.server.query_and_chat.models import UpdateChatSessionThreadRequest
 from onyx.server.query_and_chat.session_loading import (
@@ -570,6 +575,46 @@ def handle_send_chat_message(
     if get_hashed_api_key_from_request(request) or get_hashed_pat_from_request(request):
         chat_message_req.origin = MessageOrigin.API
 
+    # Multi-model streaming path: 2-3 LLMs in parallel (streaming only)
+    is_multi_model = (
+        chat_message_req.llm_overrides is not None
+        and len(chat_message_req.llm_overrides) > 1
+    )
+    if is_multi_model and chat_message_req.stream:
+        # Narrowed here; is_multi_model already checked llm_overrides is not None
+        llm_overrides = chat_message_req.llm_overrides or []
+
+        def multi_model_stream_generator() -> Generator[str, None, None]:
+            try:
+                with get_session_with_current_tenant() as db_session:
+                    for obj in handle_multi_model_stream(
+                        new_msg_req=chat_message_req,
+                        user=user,
+                        db_session=db_session,
+                        llm_overrides=llm_overrides,
+                        litellm_additional_headers=extract_headers(
+                            request.headers, LITELLM_PASS_THROUGH_HEADERS
+                        ),
+                        custom_tool_additional_headers=get_custom_tool_additional_request_headers(
+                            request.headers
+                        ),
+                        mcp_headers=chat_message_req.mcp_headers,
+                    ):
+                        yield get_json_line(obj.model_dump())
+            except Exception as e:
+                logger.exception("Error in multi-model streaming")
+                yield json.dumps({"error": str(e)})
+
+        return StreamingResponse(
+            multi_model_stream_generator(), media_type="text/event-stream"
+        )
+
+    if is_multi_model and not chat_message_req.stream:
+        raise OnyxError(
+            OnyxErrorCode.INVALID_INPUT,
+            "Multi-model mode (llm_overrides with >1 entry) requires stream=True.",
+        )
+
     # Non-streaming path: consume all packets and return complete response
     if not chat_message_req.stream:
         with get_session_with_current_tenant() as db_session:
@@ -660,6 +705,30 @@ def set_message_as_latest(
     )
 
 
+@router.put("/set-preferred-response")
+def set_preferred_response_endpoint(
+    request_body: SetPreferredResponseRequest,
+    user: User | None = Depends(current_user),
+    db_session: Session = Depends(get_session),
+) -> None:
+    """Set the preferred assistant response for a multi-model turn."""
+    try:
+        # Ownership check: get_chat_message raises ValueError if the message
+        # doesn't belong to this user, preventing cross-user mutation.
+        get_chat_message(
+            chat_message_id=request_body.user_message_id,
+            user_id=user.id if user else None,
+            db_session=db_session,
+        )
+        set_preferred_response(
+            db_session=db_session,
+            user_message_id=request_body.user_message_id,
+            preferred_assistant_message_id=request_body.preferred_response_id,
+        )
+    except ValueError as e:
+        raise OnyxError(OnyxErrorCode.INVALID_INPUT, str(e))
+
+
 @router.post("/create-chat-message-feedback")
 def create_chat_feedback(
     feedback: ChatFeedbackRequest,

backend/onyx/server/saml.py

@@ -70,7 +70,7 @@ async def upsert_saml_user(email: str) -> User:
                 try:
                     user = await user_manager.get_by_email(email)
                     # If user has a non-authenticated role, treat as non-existent
-                    if not user.role.is_web_login():
+                    if not user.account_type.is_web_login():
                         raise exceptions.UserNotExists()
                     return user
                 except exceptions.UserNotExists:

backend/tests/external_dependency_unit/conftest.py

@@ -7,6 +7,7 @@ from sqlalchemy.orm import Session
 
 from onyx.db.engine.sql_engine import get_session_with_current_tenant
 from onyx.db.engine.sql_engine import SqlEngine
+from onyx.db.enums import AccountType
 from onyx.db.models import User
 from onyx.db.models import UserRole
 from onyx.file_store.file_store import get_default_file_store
@@ -52,7 +53,12 @@ def tenant_context() -> Generator[None, None, None]:
         CURRENT_TENANT_ID_CONTEXTVAR.reset(token)
 
 
-def create_test_user(db_session: Session, email_prefix: str) -> User:
+def create_test_user(
+    db_session: Session,
+    email_prefix: str,
+    role: UserRole = UserRole.BASIC,
+    account_type: AccountType = AccountType.STANDARD,
+) -> User:
     """Helper to create a test user with a unique email"""
     # Use UUID to ensure unique email addresses
     unique_email = f"{email_prefix}_{uuid4().hex[:8]}@example.com"
@@ -68,7 +74,8 @@ def create_test_user(db_session: Session, email_prefix: str) -> User:
         is_active=True,
         is_superuser=False,
         is_verified=True,
-        role=UserRole.EXT_PERM_USER,
+        role=role,
+        account_type=account_type,
     )
     db_session.add(user)
     db_session.commit()

backend/tests/external_dependency_unit/connectors/google_drive/test_google_drive_group_sync.py

@@ -13,16 +13,29 @@ from onyx.access.utils import build_ext_group_name_for_onyx
 from onyx.configs.constants import DocumentSource
 from onyx.connectors.models import InputType
 from onyx.db.enums import AccessType
+from onyx.db.enums import AccountType
 from onyx.db.enums import ConnectorCredentialPairStatus
 from onyx.db.models import Connector
 from onyx.db.models import ConnectorCredentialPair
 from onyx.db.models import Credential
 from onyx.db.models import PublicExternalUserGroup
+from onyx.db.models import User
 from onyx.db.models import User__ExternalUserGroupId
+from onyx.db.models import UserRole
 from tests.external_dependency_unit.conftest import create_test_user
 from tests.external_dependency_unit.constants import TEST_TENANT_ID
 
 
+def _create_ext_perm_user(db_session: Session, name: str) -> User:
+    """Create an external-permission user for group sync tests."""
+    return create_test_user(
+        db_session,
+        name,
+        role=UserRole.EXT_PERM_USER,
+        account_type=AccountType.EXT_PERM_USER,
+    )
+
+
 def _create_test_connector_credential_pair(
     db_session: Session, source: DocumentSource = DocumentSource.GOOGLE_DRIVE
 ) -> ConnectorCredentialPair:
@@ -100,9 +113,9 @@ class TestPerformExternalGroupSync:
     def test_initial_group_sync(self, db_session: Session) -> None:
         """Test syncing external groups for the first time (initial sync)"""
         # Create test data
-        user1 = create_test_user(db_session, "user1")
-        user2 = create_test_user(db_session, "user2")
-        user3 = create_test_user(db_session, "user3")
+        user1 = _create_ext_perm_user(db_session, "user1")
+        user2 = _create_ext_perm_user(db_session, "user2")
+        user3 = _create_ext_perm_user(db_session, "user3")
         cc_pair = _create_test_connector_credential_pair(db_session)
 
         # Mock external groups data as a generator that yields the expected groups
@@ -175,9 +188,9 @@ class TestPerformExternalGroupSync:
     def test_update_existing_groups(self, db_session: Session) -> None:
         """Test updating existing groups (adding/removing users)"""
         # Create test data
-        user1 = create_test_user(db_session, "user1")
-        user2 = create_test_user(db_session, "user2")
-        user3 = create_test_user(db_session, "user3")
+        user1 = _create_ext_perm_user(db_session, "user1")
+        user2 = _create_ext_perm_user(db_session, "user2")
+        user3 = _create_ext_perm_user(db_session, "user3")
         cc_pair = _create_test_connector_credential_pair(db_session)
 
         # Initial sync with original groups
@@ -272,8 +285,8 @@ class TestPerformExternalGroupSync:
     def test_remove_groups(self, db_session: Session) -> None:
         """Test removing groups (groups that no longer exist in external system)"""
         # Create test data
-        user1 = create_test_user(db_session, "user1")
-        user2 = create_test_user(db_session, "user2")
+        user1 = _create_ext_perm_user(db_session, "user1")
+        user2 = _create_ext_perm_user(db_session, "user2")
         cc_pair = _create_test_connector_credential_pair(db_session)
 
         # Initial sync with multiple groups
@@ -357,7 +370,7 @@ class TestPerformExternalGroupSync:
     def test_empty_group_sync(self, db_session: Session) -> None:
         """Test syncing when no groups are returned (all groups removed)"""
         # Create test data
-        user1 = create_test_user(db_session, "user1")
+        user1 = _create_ext_perm_user(db_session, "user1")
         cc_pair = _create_test_connector_credential_pair(db_session)
 
         # Initial sync with groups
@@ -413,7 +426,7 @@ class TestPerformExternalGroupSync:
         # Create many test users
         users = []
         for i in range(150):  # More than the batch size of 100
-            users.append(create_test_user(db_session, f"user{i}"))
+            users.append(_create_ext_perm_user(db_session, f"user{i}"))
 
         cc_pair = _create_test_connector_credential_pair(db_session)
 
@@ -452,8 +465,8 @@ class TestPerformExternalGroupSync:
     def test_mixed_regular_and_public_groups(self, db_session: Session) -> None:
         """Test syncing a mix of regular and public groups"""
         # Create test data
-        user1 = create_test_user(db_session, "user1")
-        user2 = create_test_user(db_session, "user2")
+        user1 = _create_ext_perm_user(db_session, "user1")
+        user2 = _create_ext_perm_user(db_session, "user2")
         cc_pair = _create_test_connector_credential_pair(db_session)
 
         def mixed_group_sync_func(

backend/tests/external_dependency_unit/craft/conftest.py

@@ -9,6 +9,7 @@ from sqlalchemy.orm import Session
 
 from onyx.db.engine.sql_engine import get_session_with_current_tenant
 from onyx.db.engine.sql_engine import SqlEngine
+from onyx.db.enums import AccountType
 from onyx.db.enums import BuildSessionStatus
 from onyx.db.models import BuildSession
 from onyx.db.models import User
@@ -52,6 +53,7 @@ def test_user(db_session: Session, tenant_context: None) -> User:  # noqa: ARG00
         is_superuser=False,
         is_verified=True,
         role=UserRole.EXT_PERM_USER,
+        account_type=AccountType.EXT_PERM_USER,
     )
     db_session.add(user)
     db_session.commit()

backend/tests/external_dependency_unit/db/test_user_account_type.py

@@ -0,0 +1,51 @@
+"""
+Tests that account_type is correctly set when creating users through
+the internal DB functions: add_slack_user_if_not_exists and
+batch_add_ext_perm_user_if_not_exists.
+
+These functions are called by background workers (Slack bot, permission sync)
+and are not exposed via API endpoints, so they must be tested directly.
+"""
+
+from sqlalchemy.orm import Session
+
+from onyx.db.enums import AccountType
+from onyx.db.models import UserRole
+from onyx.db.users import add_slack_user_if_not_exists
+from onyx.db.users import batch_add_ext_perm_user_if_not_exists
+
+
+def test_slack_user_creation_sets_account_type_bot(db_session: Session) -> None:
+    """add_slack_user_if_not_exists sets account_type=BOT and role=SLACK_USER."""
+    user = add_slack_user_if_not_exists(db_session, "slack_acct_type@test.com")
+
+    assert user.role == UserRole.SLACK_USER
+    assert user.account_type == AccountType.BOT
+
+
+def test_ext_perm_user_creation_sets_account_type(db_session: Session) -> None:
+    """batch_add_ext_perm_user_if_not_exists sets account_type=EXT_PERM_USER."""
+    users = batch_add_ext_perm_user_if_not_exists(
+        db_session, ["extperm_acct_type@test.com"]
+    )
+
+    assert len(users) == 1
+    user = users[0]
+    assert user.role == UserRole.EXT_PERM_USER
+    assert user.account_type == AccountType.EXT_PERM_USER
+
+
+def test_ext_perm_to_slack_upgrade_updates_role_and_account_type(
+    db_session: Session,
+) -> None:
+    """When an EXT_PERM_USER is upgraded to slack, both role and account_type update."""
+    email = "ext_to_slack_acct_type@test.com"
+
+    # Create as ext_perm user first
+    batch_add_ext_perm_user_if_not_exists(db_session, [email])
+
+    # Now "upgrade" via slack path
+    user = add_slack_user_if_not_exists(db_session, email)
+
+    assert user.role == UserRole.SLACK_USER
+    assert user.account_type == AccountType.BOT

backend/tests/external_dependency_unit/llm/test_llm_provider_called.py

@@ -8,6 +8,7 @@ import pytest
 from fastapi_users.password import PasswordHelper
 from sqlalchemy.orm import Session
 
+from onyx.db.enums import AccountType
 from onyx.db.llm import fetch_existing_llm_provider
 from onyx.db.llm import remove_llm_provider
 from onyx.db.llm import update_default_provider
@@ -46,6 +47,7 @@ def _create_admin(db_session: Session) -> User:
         is_superuser=True,
         is_verified=True,
         role=UserRole.ADMIN,
+        account_type=AccountType.STANDARD,
     )
     db_session.add(user)
     db_session.commit()

backend/tests/integration/common_utils/managers/user.py

@@ -126,6 +126,15 @@ class UserManager:
 
         return test_user
 
+    @staticmethod
+    def get_permissions(user: DATestUser) -> list[str]:
+        response = requests.get(
+            url=f"{API_SERVER_URL}/me/permissions",
+            headers=user.headers,
+        )
+        response.raise_for_status()
+        return response.json()
+
     @staticmethod
     def is_role(
         user_to_verify: DATestUser,

backend/tests/integration/common_utils/managers/user_group.py

@@ -104,13 +104,30 @@ class UserGroupManager:
         )
         response.raise_for_status()
 
+    @staticmethod
+    def get_permissions(
+        user_group: DATestUserGroup,
+        user_performing_action: DATestUser,
+    ) -> list[str]:
+        response = requests.get(
+            f"{API_SERVER_URL}/manage/admin/user-group/{user_group.id}/permissions",
+            headers=user_performing_action.headers,
+        )
+        response.raise_for_status()
+        return response.json()
+
     @staticmethod
     def get_all(
         user_performing_action: DATestUser,
+        include_default: bool = False,
     ) -> list[UserGroup]:
+        params: dict[str, str] = {}
+        if include_default:
+            params["include_default"] = "true"
         response = requests.get(
             f"{API_SERVER_URL}/manage/admin/user-group",
             headers=user_performing_action.headers,
+            params=params,
         )
         response.raise_for_status()
         return [UserGroup(**ug) for ug in response.json()]

backend/tests/integration/tests/api_key/test_api_key.py

@@ -1,9 +1,13 @@
+from uuid import UUID
+
 import requests
 
 from onyx.auth.schemas import UserRole
+from onyx.db.enums import AccountType
 from tests.integration.common_utils.constants import API_SERVER_URL
 from tests.integration.common_utils.managers.api_key import APIKeyManager
 from tests.integration.common_utils.managers.user import UserManager
+from tests.integration.common_utils.managers.user_group import UserGroupManager
 from tests.integration.common_utils.test_models import DATestAPIKey
 from tests.integration.common_utils.test_models import DATestUser
 
@@ -33,3 +37,120 @@ def test_limited(reset: None) -> None:  # noqa: ARG001
         headers=api_key.headers,
     )
     assert response.status_code == 403
+
+
+def _get_service_account_account_type(
+    admin_user: DATestUser,
+    api_key_user_id: UUID,
+) -> AccountType:
+    """Fetch the account_type of a service account user via the user listing API."""
+    response = requests.get(
+        f"{API_SERVER_URL}/manage/users",
+        headers=admin_user.headers,
+        params={"include_api_keys": "true"},
+    )
+    response.raise_for_status()
+    data = response.json()
+    user_id_str = str(api_key_user_id)
+    for user in data["accepted"]:
+        if user["id"] == user_id_str:
+            return AccountType(user["account_type"])
+    raise AssertionError(
+        f"Service account user {user_id_str} not found in user listing"
+    )
+
+
+def _get_default_group_user_ids(
+    admin_user: DATestUser,
+) -> tuple[set[str], set[str]]:
+    """Return (admin_group_user_ids, basic_group_user_ids) from default groups."""
+    all_groups = UserGroupManager.get_all(
+        user_performing_action=admin_user,
+        include_default=True,
+    )
+    admin_group = next(
+        (g for g in all_groups if g.name == "Admin" and g.is_default), None
+    )
+    basic_group = next(
+        (g for g in all_groups if g.name == "Basic" and g.is_default), None
+    )
+    assert admin_group is not None, "Admin default group not found"
+    assert basic_group is not None, "Basic default group not found"
+
+    admin_ids = {str(u.id) for u in admin_group.users}
+    basic_ids = {str(u.id) for u in basic_group.users}
+    return admin_ids, basic_ids
+
+
+def test_api_key_limited_service_account(reset: None) -> None:  # noqa: ARG001
+    """LIMITED role API key: account_type is SERVICE_ACCOUNT, no group membership."""
+    admin_user: DATestUser = UserManager.create(name="admin_user")
+
+    api_key: DATestAPIKey = APIKeyManager.create(
+        api_key_role=UserRole.LIMITED,
+        user_performing_action=admin_user,
+    )
+
+    # Verify account_type
+    account_type = _get_service_account_account_type(admin_user, api_key.user_id)
+    assert (
+        account_type == AccountType.SERVICE_ACCOUNT
+    ), f"Expected account_type={AccountType.SERVICE_ACCOUNT}, got {account_type}"
+
+    # Verify no group membership
+    admin_ids, basic_ids = _get_default_group_user_ids(admin_user)
+    user_id_str = str(api_key.user_id)
+    assert (
+        user_id_str not in admin_ids
+    ), "LIMITED API key should NOT be in Admin default group"
+    assert (
+        user_id_str not in basic_ids
+    ), "LIMITED API key should NOT be in Basic default group"
+
+
+def test_api_key_basic_service_account(reset: None) -> None:  # noqa: ARG001
+    """BASIC role API key: account_type is SERVICE_ACCOUNT, in Basic group only."""
+    admin_user: DATestUser = UserManager.create(name="admin_user")
+
+    api_key: DATestAPIKey = APIKeyManager.create(
+        api_key_role=UserRole.BASIC,
+        user_performing_action=admin_user,
+    )
+
+    # Verify account_type
+    account_type = _get_service_account_account_type(admin_user, api_key.user_id)
+    assert (
+        account_type == AccountType.SERVICE_ACCOUNT
+    ), f"Expected account_type={AccountType.SERVICE_ACCOUNT}, got {account_type}"
+
+    # Verify Basic group membership
+    admin_ids, basic_ids = _get_default_group_user_ids(admin_user)
+    user_id_str = str(api_key.user_id)
+    assert user_id_str in basic_ids, "BASIC API key should be in Basic default group"
+    assert (
+        user_id_str not in admin_ids
+    ), "BASIC API key should NOT be in Admin default group"
+
+
+def test_api_key_admin_service_account(reset: None) -> None:  # noqa: ARG001
+    """ADMIN role API key: account_type is SERVICE_ACCOUNT, in Admin group only."""
+    admin_user: DATestUser = UserManager.create(name="admin_user")
+
+    api_key: DATestAPIKey = APIKeyManager.create(
+        api_key_role=UserRole.ADMIN,
+        user_performing_action=admin_user,
+    )
+
+    # Verify account_type
+    account_type = _get_service_account_account_type(admin_user, api_key.user_id)
+    assert (
+        account_type == AccountType.SERVICE_ACCOUNT
+    ), f"Expected account_type={AccountType.SERVICE_ACCOUNT}, got {account_type}"
+
+    # Verify Admin group membership
+    admin_ids, basic_ids = _get_default_group_user_ids(admin_user)
+    user_id_str = str(api_key.user_id)
+    assert user_id_str in admin_ids, "ADMIN API key should be in Admin default group"
+    assert (
+        user_id_str not in basic_ids
+    ), "ADMIN API key should NOT be in Basic default group"

backend/tests/integration/tests/auth/test_saml_user_conversion.py

@@ -4,11 +4,32 @@ import pytest
 import requests
 
 from onyx.auth.schemas import UserRole
+from onyx.db.enums import AccountType
 from tests.integration.common_utils.constants import API_SERVER_URL
 from tests.integration.common_utils.managers.user import UserManager
+from tests.integration.common_utils.managers.user_group import UserGroupManager
 from tests.integration.common_utils.test_models import DATestUser
 
 
+def _simulate_saml_login(email: str, admin_user: DATestUser) -> dict:
+    """Simulate a SAML login by calling the test upsert endpoint."""
+    response = requests.post(
+        f"{API_SERVER_URL}/manage/users/test-upsert-user",
+        json={"email": email},
+        headers=admin_user.headers,
+    )
+    response.raise_for_status()
+    return response.json()
+
+
+def _get_basic_group_member_emails(admin_user: DATestUser) -> set[str]:
+    """Get the set of emails of all members in the Basic default group."""
+    all_groups = UserGroupManager.get_all(admin_user, include_default=True)
+    basic_default = [g for g in all_groups if g.is_default and g.name == "Basic"]
+    assert basic_default, "Basic default group not found"
+    return {u.email for u in basic_default[0].users}
+
+
 @pytest.mark.skipif(
     os.environ.get("ENABLE_PAID_ENTERPRISE_EDITION_FEATURES", "").lower() != "true",
     reason="SAML tests are enterprise only",
@@ -49,15 +70,9 @@ def test_saml_user_conversion(reset: None) -> None:  # noqa: ARG001
     assert UserManager.is_role(test_user, UserRole.EXT_PERM_USER)
 
     # Simulate SAML login by calling the test endpoint
-    response = requests.post(
-        f"{API_SERVER_URL}/manage/users/test-upsert-user",
-        json={"email": test_user_email},
-        headers=admin_user.headers,  # Use admin headers for authorization
-    )
-    response.raise_for_status()
+    user_data = _simulate_saml_login(test_user_email, admin_user)
 
     # Verify the response indicates the role changed to BASIC
-    user_data = response.json()
     assert user_data["role"] == UserRole.BASIC.value
 
     # Verify user role was changed in the database
@@ -82,16 +97,237 @@ def test_saml_user_conversion(reset: None) -> None:  # noqa: ARG001
     assert UserManager.is_role(slack_user, UserRole.SLACK_USER)
 
     # Simulate SAML login again
-    response = requests.post(
-        f"{API_SERVER_URL}/manage/users/test-upsert-user",
-        json={"email": slack_user_email},
-        headers=admin_user.headers,
-    )
-    response.raise_for_status()
+    user_data = _simulate_saml_login(slack_user_email, admin_user)
 
     # Verify the response indicates the role changed to BASIC
-    user_data = response.json()
     assert user_data["role"] == UserRole.BASIC.value
 
     # Verify the user's role was changed in the database
     assert UserManager.is_role(slack_user, UserRole.BASIC)
+
+
+@pytest.mark.skipif(
+    os.environ.get("ENABLE_PAID_ENTERPRISE_EDITION_FEATURES", "").lower() != "true",
+    reason="SAML tests are enterprise only",
+)
+def test_saml_user_conversion_sets_account_type_and_group(
+    reset: None,  # noqa: ARG001
+) -> None:
+    """
+    Test that SAML login sets account_type to STANDARD when converting a
+    non-web user (EXT_PERM_USER) and that the user receives the correct role
+    (BASIC) after conversion.
+
+    This validates the permissions-migration-phase2 changes which ensure that:
+    1. account_type is updated to 'standard' on SAML conversion
+    2. The converted user is assigned to the Basic default group
+    """
+    # Create an admin user (first user is automatically admin)
+    admin_user: DATestUser = UserManager.create(email="admin@example.com")
+
+    # Create a user and set them as EXT_PERM_USER
+    test_email = "ext_convert@example.com"
+    test_user = UserManager.create(email=test_email)
+    UserManager.set_role(
+        user_to_set=test_user,
+        target_role=UserRole.EXT_PERM_USER,
+        user_performing_action=admin_user,
+        explicit_override=True,
+    )
+    assert UserManager.is_role(test_user, UserRole.EXT_PERM_USER)
+
+    # Simulate SAML login
+    user_data = _simulate_saml_login(test_email, admin_user)
+
+    # Verify account_type is set to standard after conversion
+    assert (
+        user_data["account_type"] == AccountType.STANDARD.value
+    ), f"Expected account_type='{AccountType.STANDARD.value}', got '{user_data['account_type']}'"
+
+    # Verify role is BASIC after conversion
+    assert user_data["role"] == UserRole.BASIC.value
+
+    # Verify the user was assigned to the Basic default group
+    assert test_email in _get_basic_group_member_emails(
+        admin_user
+    ), f"Converted user '{test_email}' not found in Basic default group"
+
+
+@pytest.mark.skipif(
+    os.environ.get("ENABLE_PAID_ENTERPRISE_EDITION_FEATURES", "").lower() != "true",
+    reason="SAML tests are enterprise only",
+)
+def test_saml_normal_signin_assigns_group(
+    reset: None,  # noqa: ARG001
+) -> None:
+    """
+    Test that a brand-new user signing in via SAML for the first time
+    is created with the correct role, account_type, and group membership.
+
+    This validates that normal SAML sign-in (not an upgrade from
+    SLACK_USER/EXT_PERM_USER) correctly:
+    1. Creates the user with role=BASIC and account_type=STANDARD
+    2. Assigns the user to the Basic default group
+    """
+    # First user becomes admin
+    admin_user: DATestUser = UserManager.create(email="admin@example.com")
+
+    # New user signs in via SAML (no prior account)
+    new_email = "new_saml_user@example.com"
+    user_data = _simulate_saml_login(new_email, admin_user)
+
+    # Verify role and account_type
+    assert user_data["role"] == UserRole.BASIC.value
+    assert user_data["account_type"] == AccountType.STANDARD.value
+
+    # Verify user is in the Basic default group
+    assert new_email in _get_basic_group_member_emails(
+        admin_user
+    ), f"New SAML user '{new_email}' not found in Basic default group"
+
+
+@pytest.mark.skipif(
+    os.environ.get("ENABLE_PAID_ENTERPRISE_EDITION_FEATURES", "").lower() != "true",
+    reason="SAML tests are enterprise only",
+)
+def test_saml_user_conversion_restores_group_membership(
+    reset: None,  # noqa: ARG001
+) -> None:
+    """
+    Test that SAML login restores Basic group membership when converting
+    a non-authenticated user (EXT_PERM_USER or SLACK_USER) to BASIC.
+
+    Group membership implies 'basic' permission (verified by
+    test_new_group_gets_basic_permission).
+    """
+    admin_user: DATestUser = UserManager.create(email="admin@example.com")
+
+    # --- EXT_PERM_USER path ---
+    ext_email = "ext_perm_perms@example.com"
+    ext_user = UserManager.create(email=ext_email)
+    assert ext_email in _get_basic_group_member_emails(admin_user)
+
+    UserManager.set_role(
+        user_to_set=ext_user,
+        target_role=UserRole.EXT_PERM_USER,
+        user_performing_action=admin_user,
+        explicit_override=True,
+    )
+    assert ext_email not in _get_basic_group_member_emails(admin_user)
+
+    user_data = _simulate_saml_login(ext_email, admin_user)
+    assert user_data["role"] == UserRole.BASIC.value
+    assert ext_email in _get_basic_group_member_emails(
+        admin_user
+    ), "EXT_PERM_USER should be back in Basic group after SAML conversion"
+
+    # --- SLACK_USER path ---
+    slack_email = "slack_perms@example.com"
+    slack_user = UserManager.create(email=slack_email)
+
+    UserManager.set_role(
+        user_to_set=slack_user,
+        target_role=UserRole.SLACK_USER,
+        user_performing_action=admin_user,
+        explicit_override=True,
+    )
+    assert slack_email not in _get_basic_group_member_emails(admin_user)
+
+    user_data = _simulate_saml_login(slack_email, admin_user)
+    assert user_data["role"] == UserRole.BASIC.value
+    assert slack_email in _get_basic_group_member_emails(
+        admin_user
+    ), "SLACK_USER should be back in Basic group after SAML conversion"
+
+
+@pytest.mark.skipif(
+    os.environ.get("ENABLE_PAID_ENTERPRISE_EDITION_FEATURES", "").lower() != "true",
+    reason="SAML tests are enterprise only",
+)
+def test_saml_round_trip_group_lifecycle(
+    reset: None,  # noqa: ARG001
+) -> None:
+    """
+    Test the full round-trip: BASIC -> EXT_PERM -> SAML(BASIC) -> EXT_PERM -> SAML(BASIC).
+
+    Verifies group membership is correctly removed and restored at each transition.
+    """
+    admin_user: DATestUser = UserManager.create(email="admin@example.com")
+
+    test_email = "roundtrip@example.com"
+    test_user = UserManager.create(email=test_email)
+
+    # Step 1: BASIC user is in Basic group
+    assert test_email in _get_basic_group_member_emails(admin_user)
+
+    # Step 2: Downgrade to EXT_PERM_USER — loses Basic group
+    UserManager.set_role(
+        user_to_set=test_user,
+        target_role=UserRole.EXT_PERM_USER,
+        user_performing_action=admin_user,
+        explicit_override=True,
+    )
+    assert test_email not in _get_basic_group_member_emails(admin_user)
+
+    # Step 3: SAML login — converts back to BASIC, regains Basic group
+    _simulate_saml_login(test_email, admin_user)
+    assert test_email in _get_basic_group_member_emails(
+        admin_user
+    ), "Should be in Basic group after first SAML conversion"
+
+    # Step 4: Downgrade again
+    UserManager.set_role(
+        user_to_set=test_user,
+        target_role=UserRole.EXT_PERM_USER,
+        user_performing_action=admin_user,
+        explicit_override=True,
+    )
+    assert test_email not in _get_basic_group_member_emails(admin_user)
+
+    # Step 5: SAML login again — should still restore correctly
+    _simulate_saml_login(test_email, admin_user)
+    assert test_email in _get_basic_group_member_emails(
+        admin_user
+    ), "Should be in Basic group after second SAML conversion"
+
+
+@pytest.mark.skipif(
+    os.environ.get("ENABLE_PAID_ENTERPRISE_EDITION_FEATURES", "").lower() != "true",
+    reason="SAML tests are enterprise only",
+)
+def test_saml_slack_user_conversion_sets_account_type_and_group(
+    reset: None,  # noqa: ARG001
+) -> None:
+    """
+    Test that SAML login sets account_type to STANDARD and assigns Basic group
+    when converting a SLACK_USER (BOT account_type).
+
+    Mirrors test_saml_user_conversion_sets_account_type_and_group but for
+    SLACK_USER instead of EXT_PERM_USER, and additionally verifies permissions.
+    """
+    admin_user: DATestUser = UserManager.create(email="admin@example.com")
+
+    test_email = "slack_convert@example.com"
+    test_user = UserManager.create(email=test_email)
+
+    UserManager.set_role(
+        user_to_set=test_user,
+        target_role=UserRole.SLACK_USER,
+        user_performing_action=admin_user,
+        explicit_override=True,
+    )
+    assert UserManager.is_role(test_user, UserRole.SLACK_USER)
+
+    # SAML login
+    user_data = _simulate_saml_login(test_email, admin_user)
+
+    # Verify account_type and role
+    assert (
+        user_data["account_type"] == AccountType.STANDARD.value
+    ), f"Expected STANDARD, got {user_data['account_type']}"
+    assert user_data["role"] == UserRole.BASIC.value
+
+    # Verify Basic group membership (implies 'basic' permission)
+    assert test_email in _get_basic_group_member_emails(
+        admin_user
+    ), f"Converted SLACK_USER '{test_email}' not found in Basic default group"

backend/tests/integration/tests/permissions/test_auth_permission_propagation.py

@@ -0,0 +1,82 @@
+"""Integration tests for permission propagation across auth-triggered group changes.
+
+These tests verify that effective permissions (via /me/permissions) actually
+propagate when users are added/removed from default groups through role changes.
+Custom permission grant tests will be added once the permission grant API is built.
+"""
+
+import os
+
+import pytest
+
+from onyx.auth.schemas import UserRole
+from tests.integration.common_utils.managers.user import UserManager
+from tests.integration.common_utils.managers.user_group import UserGroupManager
+from tests.integration.common_utils.test_models import DATestUser
+
+
+def _get_basic_group_member_emails(admin_user: DATestUser) -> set[str]:
+    all_groups = UserGroupManager.get_all(admin_user, include_default=True)
+    basic_group = next(
+        (g for g in all_groups if g.is_default and g.name == "Basic"), None
+    )
+    assert basic_group is not None, "Basic default group not found"
+    return {u.email for u in basic_group.users}
+
+
+@pytest.mark.skipif(
+    os.environ.get("ENABLE_PAID_ENTERPRISE_EDITION_FEATURES", "").lower() != "true",
+    reason="Permission propagation tests require enterprise features",
+)
+def test_basic_permission_granted_on_registration(
+    reset: None,  # noqa: ARG001
+) -> None:
+    """New users should get 'basic' permission through default group assignment."""
+    admin_user: DATestUser = UserManager.create(email="admin@example.com")
+    basic_user: DATestUser = UserManager.create(email="basic@example.com")
+
+    # Admin should have permissions from Admin group
+    admin_perms = UserManager.get_permissions(admin_user)
+    assert "basic" in admin_perms
+
+    # Basic user should have 'basic' from Basic default group
+    basic_perms = UserManager.get_permissions(basic_user)
+    assert "basic" in basic_perms
+
+    # Verify group membership matches
+    assert basic_user.email in _get_basic_group_member_emails(admin_user)
+
+
+@pytest.mark.skipif(
+    os.environ.get("ENABLE_PAID_ENTERPRISE_EDITION_FEATURES", "").lower() != "true",
+    reason="Permission propagation tests require enterprise features",
+)
+def test_role_downgrade_removes_basic_group_and_permission(
+    reset: None,  # noqa: ARG001
+) -> None:
+    """Downgrading to EXT_PERM_USER or SLACK_USER should remove from Basic group."""
+    admin_user: DATestUser = UserManager.create(email="admin@example.com")
+
+    # --- EXT_PERM_USER ---
+    ext_user: DATestUser = UserManager.create(email="ext@example.com")
+    assert ext_user.email in _get_basic_group_member_emails(admin_user)
+
+    UserManager.set_role(
+        user_to_set=ext_user,
+        target_role=UserRole.EXT_PERM_USER,
+        user_performing_action=admin_user,
+        explicit_override=True,
+    )
+    assert ext_user.email not in _get_basic_group_member_emails(admin_user)
+
+    # --- SLACK_USER ---
+    slack_user: DATestUser = UserManager.create(email="slack@example.com")
+    assert slack_user.email in _get_basic_group_member_emails(admin_user)
+
+    UserManager.set_role(
+        user_to_set=slack_user,
+        target_role=UserRole.SLACK_USER,
+        user_performing_action=admin_user,
+        explicit_override=True,
+    )
+    assert slack_user.email not in _get_basic_group_member_emails(admin_user)

backend/tests/integration/tests/scim/test_scim_groups.py

@@ -21,8 +21,15 @@ import pytest
 import requests
 
 from onyx.auth.schemas import UserRole
+from tests.integration.common_utils.constants import ADMIN_USER_NAME
+from tests.integration.common_utils.constants import API_SERVER_URL
+from tests.integration.common_utils.constants import GENERAL_HEADERS
 from tests.integration.common_utils.managers.scim_client import ScimClient
 from tests.integration.common_utils.managers.scim_token import ScimTokenManager
+from tests.integration.common_utils.managers.user import build_email
+from tests.integration.common_utils.managers.user import DEFAULT_PASSWORD
+from tests.integration.common_utils.managers.user import UserManager
+from tests.integration.common_utils.test_models import DATestUser
 
 
 SCIM_GROUP_SCHEMA = "urn:ietf:params:scim:schemas:core:2.0:Group"
@@ -44,13 +51,6 @@ def scim_token(idp_style: str) -> str:
     per IdP-style run and reuse. Uses UserManager directly to avoid
     fixture-scope conflicts with the function-scoped admin_user fixture.
     """
-    from tests.integration.common_utils.constants import ADMIN_USER_NAME
-    from tests.integration.common_utils.constants import GENERAL_HEADERS
-    from tests.integration.common_utils.managers.user import build_email
-    from tests.integration.common_utils.managers.user import DEFAULT_PASSWORD
-    from tests.integration.common_utils.managers.user import UserManager
-    from tests.integration.common_utils.test_models import DATestUser
-
     try:
         admin = UserManager.create(name=ADMIN_USER_NAME)
     except Exception:
@@ -550,3 +550,145 @@ def test_patch_add_duplicate_member_is_idempotent(
     )
     assert resp.status_code == 200
     assert len(resp.json()["members"]) == 1  # still just one member
+
+
+def test_create_group_reserved_name_admin(scim_token: str) -> None:
+    """POST /Groups with reserved name 'Admin' returns 409."""
+    resp = _create_scim_group(scim_token, "Admin", external_id="ext-reserved-admin")
+    assert resp.status_code == 409
+    assert "reserved" in resp.json()["detail"].lower()
+
+
+def test_create_group_reserved_name_basic(scim_token: str) -> None:
+    """POST /Groups with reserved name 'Basic' returns 409."""
+    resp = _create_scim_group(scim_token, "Basic", external_id="ext-reserved-basic")
+    assert resp.status_code == 409
+    assert "reserved" in resp.json()["detail"].lower()
+
+
+def test_replace_group_cannot_rename_to_reserved(
+    scim_token: str, idp_style: str
+) -> None:
+    """PUT /Groups/{id} renaming a group to 'Admin' returns 409."""
+    created = _create_scim_group(
+        scim_token,
+        f"Rename To Reserved {idp_style}",
+        external_id=f"ext-rtr-{idp_style}",
+    ).json()
+
+    resp = ScimClient.put(
+        f"/Groups/{created['id']}",
+        scim_token,
+        json=_make_group_resource(
+            display_name="Admin", external_id=f"ext-rtr-{idp_style}"
+        ),
+    )
+    assert resp.status_code == 409
+    assert "reserved" in resp.json()["detail"].lower()
+
+
+def test_patch_rename_to_reserved_name(scim_token: str, idp_style: str) -> None:
+    """PATCH /Groups/{id} renaming a group to 'Basic' returns 409."""
+    created = _create_scim_group(
+        scim_token,
+        f"Patch Rename Reserved {idp_style}",
+        external_id=f"ext-prr-{idp_style}",
+    ).json()
+
+    resp = ScimClient.patch(
+        f"/Groups/{created['id']}",
+        scim_token,
+        json=_make_patch_request(
+            [{"op": "replace", "path": "displayName", "value": "Basic"}],
+            idp_style,
+        ),
+    )
+    assert resp.status_code == 409
+    assert "reserved" in resp.json()["detail"].lower()
+
+
+def test_delete_reserved_group_rejected(scim_token: str) -> None:
+    """DELETE /Groups/{id} on a reserved group ('Admin') returns 409."""
+    # Look up the reserved 'Admin' group via SCIM filter
+    resp = ScimClient.get('/Groups?filter=displayName eq "Admin"', scim_token)
+    assert resp.status_code == 200
+    resources = resp.json()["Resources"]
+    assert len(resources) >= 1, "Expected reserved 'Admin' group to exist"
+    admin_group_id = resources[0]["id"]
+
+    resp = ScimClient.delete(f"/Groups/{admin_group_id}", scim_token)
+    assert resp.status_code == 409
+    assert "reserved" in resp.json()["detail"].lower()
+
+
+def test_scim_created_group_has_basic_permission(
+    scim_token: str, idp_style: str
+) -> None:
+    """POST /Groups assigns the 'basic' permission to the group itself."""
+    # Create a SCIM group (no members needed — we check the group's permissions)
+    resp = _create_scim_group(
+        scim_token,
+        f"Basic Perm Group {idp_style}",
+        external_id=f"ext-basic-perm-{idp_style}",
+    )
+    assert resp.status_code == 201
+    group_id = resp.json()["id"]
+
+    # Log in as the admin user (created by the scim_token fixture).
+    admin = DATestUser(
+        id="",
+        email=build_email(ADMIN_USER_NAME),
+        password=DEFAULT_PASSWORD,
+        headers=GENERAL_HEADERS,
+        role=UserRole.ADMIN,
+        is_active=True,
+    )
+    admin = UserManager.login_as_user(admin)
+
+    # Verify the group itself was granted the basic permission
+    perms_resp = requests.get(
+        f"{API_SERVER_URL}/manage/admin/user-group/{group_id}/permissions",
+        headers=admin.headers,
+    )
+    perms_resp.raise_for_status()
+    perms = perms_resp.json()
+    assert "basic" in perms, f"SCIM group should have 'basic' permission, got: {perms}"
+
+
+def test_replace_group_cannot_rename_from_reserved(scim_token: str) -> None:
+    """PUT /Groups/{id} renaming a reserved group ('Admin') to a non-reserved name returns 409."""
+    resp = ScimClient.get('/Groups?filter=displayName eq "Admin"', scim_token)
+    assert resp.status_code == 200
+    resources = resp.json()["Resources"]
+    assert len(resources) >= 1, "Expected reserved 'Admin' group to exist"
+    admin_group_id = resources[0]["id"]
+
+    resp = ScimClient.put(
+        f"/Groups/{admin_group_id}",
+        scim_token,
+        json=_make_group_resource(
+            display_name="RenamedAdmin", external_id="ext-rename-from-reserved"
+        ),
+    )
+    assert resp.status_code == 409
+    assert "reserved" in resp.json()["detail"].lower()
+
+
+def test_patch_rename_from_reserved_name(scim_token: str, idp_style: str) -> None:
+    """PATCH /Groups/{id} renaming a reserved group ('Admin') returns 409."""
+    resp = ScimClient.get('/Groups?filter=displayName eq "Admin"', scim_token)
+    assert resp.status_code == 200
+    resources = resp.json()["Resources"]
+    assert len(resources) >= 1, "Expected reserved 'Admin' group to exist"
+    admin_group_id = resources[0]["id"]
+
+    resp = ScimClient.patch(
+        f"/Groups/{admin_group_id}",
+        scim_token,
+        json=_make_patch_request(
+            [{"op": "replace", "path": "displayName", "value": "RenamedAdmin"}],
+            idp_style,
+        ),
+    )
+    assert resp.status_code == 409
+    assert "reserved" in resp.json()["detail"].lower()

backend/tests/integration/tests/scim/test_scim_users.py

@@ -35,9 +35,16 @@ from onyx.auth.schemas import UserRole
 from onyx.configs.app_configs import REDIS_DB_NUMBER
 from onyx.configs.app_configs import REDIS_HOST
 from onyx.configs.app_configs import REDIS_PORT
+from onyx.db.enums import AccountType
 from onyx.server.settings.models import ApplicationStatus
+from tests.integration.common_utils.constants import ADMIN_USER_NAME
+from tests.integration.common_utils.constants import GENERAL_HEADERS
 from tests.integration.common_utils.managers.scim_client import ScimClient
 from tests.integration.common_utils.managers.scim_token import ScimTokenManager
+from tests.integration.common_utils.managers.user import build_email
+from tests.integration.common_utils.managers.user import DEFAULT_PASSWORD
+from tests.integration.common_utils.managers.user import UserManager
+from tests.integration.common_utils.test_models import DATestUser
 
 
 SCIM_USER_SCHEMA = "urn:ietf:params:scim:schemas:core:2.0:User"
@@ -211,6 +218,49 @@ def test_create_user(scim_token: str, idp_style: str) -> None:
         _assert_entra_emails(body, email)
 
 
+def test_create_user_default_group_and_account_type(
+    scim_token: str, idp_style: str
+) -> None:
+    """SCIM-provisioned users get Basic default group and STANDARD account_type."""
+    email = f"scim_defaults_{idp_style}@example.com"
+    ext_id = f"ext-defaults-{idp_style}"
+    resp = _create_scim_user(scim_token, email, ext_id, idp_style)
+    assert resp.status_code == 201
+    user_id = resp.json()["id"]
+
+    # --- Verify group assignment via SCIM GET ---
+    get_resp = ScimClient.get(f"/Users/{user_id}", scim_token)
+    assert get_resp.status_code == 200
+    groups = get_resp.json().get("groups", [])
+    group_names = {g["display"] for g in groups}
+    assert "Basic" in group_names, f"Expected 'Basic' in groups, got {group_names}"
+    assert "Admin" not in group_names, "SCIM user should not be in Admin group"
+
+    # --- Verify account_type via admin API ---
+    admin = UserManager.login_as_user(
+        DATestUser(
+            id="",
+            email=build_email(ADMIN_USER_NAME),
+            password=DEFAULT_PASSWORD,
+            headers=GENERAL_HEADERS,
+            role=UserRole.ADMIN,
+            is_active=True,
+        )
+    )
+    page = UserManager.get_user_page(
+        user_performing_action=admin,
+        search_query=email,
+    )
+    assert page.total_items >= 1
+    scim_user_snapshot = next((u for u in page.items if u.email == email), None)
+    assert (
+        scim_user_snapshot is not None
+    ), f"SCIM user {email} not found in user listing"
+    assert (
+        scim_user_snapshot.account_type == AccountType.STANDARD
+    ), f"Expected STANDARD, got {scim_user_snapshot.account_type}"
+
+
 def test_get_user(scim_token: str, idp_style: str) -> None:
     """GET /Users/{id} returns the user resource with all stored fields."""
     email = f"scim_get_{idp_style}@example.com"

backend/tests/integration/tests/usergroup/test_group_membership_updates_user_permissions.py

@@ -0,0 +1,118 @@
+import os
+
+import pytest
+
+from onyx.db.engine.sql_engine import get_session_with_current_tenant
+from onyx.db.enums import Permission
+from onyx.db.models import PermissionGrant
+from onyx.db.models import UserGroup as UserGroupModel
+from onyx.db.permissions import recompute_permissions_for_group__no_commit
+from onyx.db.permissions import recompute_user_permissions__no_commit
+from tests.integration.common_utils.managers.user import UserManager
+from tests.integration.common_utils.managers.user_group import UserGroupManager
+from tests.integration.common_utils.test_models import DATestUser
+
+
+@pytest.mark.skipif(
+    os.environ.get("ENABLE_PAID_ENTERPRISE_EDITION_FEATURES", "").lower() != "true",
+    reason="User group tests are enterprise only",
+)
+def test_user_gets_permissions_when_added_to_group(
+    reset: None,  # noqa: ARG001
+) -> None:
+    admin_user: DATestUser = UserManager.create(name="admin_for_perm_test")
+    basic_user: DATestUser = UserManager.create(name="basic_user_for_perm_test")
+
+    # basic_user starts with only "basic" from the default group
+    initial_permissions = UserManager.get_permissions(basic_user)
+    assert "basic" in initial_permissions
+    assert "add:agents" not in initial_permissions
+
+    # Create a new group and add basic_user
+    group = UserGroupManager.create(
+        name="perm-test-group",
+        user_ids=[admin_user.id, basic_user.id],
+        user_performing_action=admin_user,
+    )
+
+    # Grant a non-basic permission to the group and recompute
+    with get_session_with_current_tenant() as db_session:
+        db_group = db_session.get(UserGroupModel, group.id)
+        assert db_group is not None
+        db_session.add(
+            PermissionGrant(
+                group_id=db_group.id,
+                permission=Permission.ADD_AGENTS,
+                grant_source="SYSTEM",
+            )
+        )
+        db_session.flush()
+        recompute_user_permissions__no_commit(basic_user.id, db_session)
+        db_session.commit()
+
+    # Verify the user gained the new permission (expanded includes read:agents)
+    updated_permissions = UserManager.get_permissions(basic_user)
+    assert (
+        "add:agents" in updated_permissions
+    ), f"User should have 'add:agents' after group grant, got: {updated_permissions}"
+    assert (
+        "read:agents" in updated_permissions
+    ), f"User should have implied 'read:agents', got: {updated_permissions}"
+    assert "basic" in updated_permissions
+
+
+@pytest.mark.skipif(
+    os.environ.get("ENABLE_PAID_ENTERPRISE_EDITION_FEATURES", "").lower() != "true",
+    reason="User group tests are enterprise only",
+)
+def test_group_permission_change_propagates_to_all_members(
+    reset: None,  # noqa: ARG001
+) -> None:
+    admin_user: DATestUser = UserManager.create(name="admin_propagate")
+    user_a: DATestUser = UserManager.create(name="user_a_propagate")
+    user_b: DATestUser = UserManager.create(name="user_b_propagate")
+
+    group = UserGroupManager.create(
+        name="propagate-test-group",
+        user_ids=[admin_user.id, user_a.id, user_b.id],
+        user_performing_action=admin_user,
+    )
+
+    # Neither user should have add:agents yet
+    for u in (user_a, user_b):
+        assert "add:agents" not in UserManager.get_permissions(u)
+
+    # Grant add:agents to the group, then batch-recompute
+    with get_session_with_current_tenant() as db_session:
+        grant = PermissionGrant(
+            group_id=group.id,
+            permission=Permission.ADD_AGENTS,
+            grant_source="SYSTEM",
+        )
+        db_session.add(grant)
+        db_session.flush()
+        recompute_permissions_for_group__no_commit(group.id, db_session)
+        db_session.commit()
+
+    # Both users should now have the permission (plus implied read:agents)
+    for u in (user_a, user_b):
+        perms = UserManager.get_permissions(u)
+        assert "add:agents" in perms, f"{u.id} missing add:agents: {perms}"
+        assert "read:agents" in perms, f"{u.id} missing implied read:agents: {perms}"
+
+    # Soft-delete the grant and recompute — permission should be removed
+    with get_session_with_current_tenant() as db_session:
+        db_grant = (
+            db_session.query(PermissionGrant)
+            .filter_by(group_id=group.id, permission=Permission.ADD_AGENTS)
+            .first()
+        )
+        assert db_grant is not None
+        db_grant.is_deleted = True
+        db_session.flush()
+        recompute_permissions_for_group__no_commit(group.id, db_session)
+        db_session.commit()
+
+    for u in (user_a, user_b):
+        perms = UserManager.get_permissions(u)
+        assert "add:agents" not in perms, f"{u.id} still has add:agents: {perms}"

backend/tests/integration/tests/usergroup/test_new_group_gets_basic_permission.py

@@ -0,0 +1,30 @@
+import os
+
+import pytest
+
+from tests.integration.common_utils.managers.user import UserManager
+from tests.integration.common_utils.managers.user_group import UserGroupManager
+from tests.integration.common_utils.test_models import DATestUser
+
+
+@pytest.mark.skipif(
+    os.environ.get("ENABLE_PAID_ENTERPRISE_EDITION_FEATURES", "").lower() != "true",
+    reason="User group tests are enterprise only",
+)
+def test_new_group_gets_basic_permission(reset: None) -> None:  # noqa: ARG001
+    admin_user: DATestUser = UserManager.create(name="admin_for_basic_perm")
+
+    user_group = UserGroupManager.create(
+        name="basic-perm-test-group",
+        user_ids=[admin_user.id],
+        user_performing_action=admin_user,
+    )
+
+    permissions = UserGroupManager.get_permissions(
+        user_group=user_group,
+        user_performing_action=admin_user,
+    )
+
+    assert (
+        "basic" in permissions
+    ), f"New group should have 'basic' permission, got: {permissions}"

backend/tests/integration/tests/users/test_default_group_assignment.py

@@ -0,0 +1,78 @@
+"""Integration tests for default group assignment on user registration.
+
+Verifies that:
+- The first registered user is assigned to the Admin default group
+- Subsequent registered users are assigned to the Basic default group
+- account_type is set to STANDARD for email/password registrations
+"""
+
+from onyx.auth.schemas import UserRole
+from onyx.db.enums import AccountType
+from tests.integration.common_utils.managers.user import UserManager
+from tests.integration.common_utils.managers.user_group import UserGroupManager
+from tests.integration.common_utils.test_models import DATestUser
+
+
+def test_default_group_assignment_on_registration(reset: None) -> None:  # noqa: ARG001
+    # Register first user — should become admin
+    admin_user: DATestUser = UserManager.create(name="first_user")
+    assert admin_user.role == UserRole.ADMIN
+
+    # Register second user — should become basic
+    basic_user: DATestUser = UserManager.create(name="second_user")
+    assert basic_user.role == UserRole.BASIC
+
+    # Fetch all groups including default ones
+    all_groups = UserGroupManager.get_all(
+        user_performing_action=admin_user,
+        include_default=True,
+    )
+
+    # Find the default Admin and Basic groups
+    admin_group = next(
+        (g for g in all_groups if g.name == "Admin" and g.is_default), None
+    )
+    basic_group = next(
+        (g for g in all_groups if g.name == "Basic" and g.is_default), None
+    )
+    assert admin_group is not None, "Admin default group not found"
+    assert basic_group is not None, "Basic default group not found"
+
+    # Verify admin user is in Admin group and NOT in Basic group
+    admin_group_user_ids = {str(u.id) for u in admin_group.users}
+    basic_group_user_ids = {str(u.id) for u in basic_group.users}
+
+    assert (
+        admin_user.id in admin_group_user_ids
+    ), "First user should be in Admin default group"
+    assert (
+        admin_user.id not in basic_group_user_ids
+    ), "First user should NOT be in Basic default group"
+
+    # Verify basic user is in Basic group and NOT in Admin group
+    assert (
+        basic_user.id in basic_group_user_ids
+    ), "Second user should be in Basic default group"
+    assert (
+        basic_user.id not in admin_group_user_ids
+    ), "Second user should NOT be in Admin default group"
+
+    # Verify account_type is STANDARD for both users via user listing API
+    paginated_result = UserManager.get_user_page(
+        user_performing_action=admin_user,
+        page_num=0,
+        page_size=10,
+    )
+    users_by_id = {str(u.id): u for u in paginated_result.items}
+
+    admin_snapshot = users_by_id.get(admin_user.id)
+    basic_snapshot = users_by_id.get(basic_user.id)
+    assert admin_snapshot is not None, "Admin user not found in user listing"
+    assert basic_snapshot is not None, "Basic user not found in user listing"
+
+    assert (
+        admin_snapshot.account_type == AccountType.STANDARD
+    ), f"Admin user account_type should be STANDARD, got {admin_snapshot.account_type}"
+    assert (
+        basic_snapshot.account_type == AccountType.STANDARD
+    ), f"Basic user account_type should be STANDARD, got {basic_snapshot.account_type}"

backend/tests/integration/tests/users/test_password_signup_upgrade.py

@@ -0,0 +1,135 @@
+"""Integration tests for password signup upgrade paths.
+
+Verifies that when a BOT or EXT_PERM_USER user signs up via email/password:
+- Their account_type is upgraded to STANDARD
+- They are assigned to the Basic default group
+- They gain the correct effective permissions
+"""
+
+import pytest
+
+from onyx.auth.schemas import UserRole
+from onyx.db.enums import AccountType
+from tests.integration.common_utils.managers.user import UserManager
+from tests.integration.common_utils.managers.user_group import UserGroupManager
+from tests.integration.common_utils.test_models import DATestUser
+
+
+def _get_default_group_member_emails(
+    admin_user: DATestUser,
+    group_name: str,
+) -> set[str]:
+    """Get the set of emails of all members in a named default group."""
+    all_groups = UserGroupManager.get_all(admin_user, include_default=True)
+    matched = [g for g in all_groups if g.is_default and g.name == group_name]
+    assert matched, f"Default group '{group_name}' not found"
+    return {u.email for u in matched[0].users}
+
+
+@pytest.mark.parametrize(
+    "target_role",
+    [UserRole.EXT_PERM_USER, UserRole.SLACK_USER],
+    ids=["ext_perm_user", "slack_user"],
+)
+def test_password_signup_upgrade(
+    reset: None,  # noqa: ARG001
+    target_role: UserRole,
+) -> None:
+    """When a non-web user signs up via email/password, they should be
+    upgraded to STANDARD account_type and assigned to the Basic default group."""
+    admin_user: DATestUser = UserManager.create(email="admin@example.com")
+
+    test_email = f"{target_role.value}_upgrade@example.com"
+    test_user = UserManager.create(email=test_email)
+
+    test_user = UserManager.set_role(
+        user_to_set=test_user,
+        target_role=target_role,
+        user_performing_action=admin_user,
+        explicit_override=True,
+    )
+
+    # Verify user was removed from Basic group after downgrade
+    basic_emails = _get_default_group_member_emails(admin_user, "Basic")
+    assert (
+        test_email not in basic_emails
+    ), f"{target_role.value} should not be in Basic default group"
+
+    # Re-register with the same email — triggers the password signup upgrade
+    upgraded_user = UserManager.create(email=test_email)
+
+    assert upgraded_user.role == UserRole.BASIC
+
+    paginated = UserManager.get_user_page(
+        user_performing_action=admin_user,
+        page_num=0,
+        page_size=10,
+    )
+    user_snapshot = next(
+        (u for u in paginated.items if str(u.id) == upgraded_user.id), None
+    )
+    assert user_snapshot is not None
+    assert (
+        user_snapshot.account_type == AccountType.STANDARD
+    ), f"Expected STANDARD, got {user_snapshot.account_type}"
+
+    # Verify user is now in the Basic default group
+    basic_emails = _get_default_group_member_emails(admin_user, "Basic")
+    assert (
+        test_email in basic_emails
+    ), f"Upgraded user '{test_email}' not found in Basic default group"
+
+
+def test_password_signup_upgrade_propagates_permissions(
+    reset: None,  # noqa: ARG001
+) -> None:
+    """When an EXT_PERM_USER or SLACK_USER signs up via password, they should
+    gain the 'basic' permission through the Basic default group assignment."""
+    admin_user: DATestUser = UserManager.create(email="admin@example.com")
+
+    # --- EXT_PERM_USER path ---
+    ext_email = "ext_perms_check@example.com"
+    ext_user = UserManager.create(email=ext_email)
+
+    initial_perms = UserManager.get_permissions(ext_user)
+    assert "basic" in initial_perms
+
+    ext_user = UserManager.set_role(
+        user_to_set=ext_user,
+        target_role=UserRole.EXT_PERM_USER,
+        user_performing_action=admin_user,
+        explicit_override=True,
+    )
+
+    basic_emails = _get_default_group_member_emails(admin_user, "Basic")
+    assert ext_email not in basic_emails
+
+    upgraded = UserManager.create(email=ext_email)
+    assert upgraded.role == UserRole.BASIC
+
+    perms = UserManager.get_permissions(upgraded)
+    assert (
+        "basic" in perms
+    ), f"Upgraded EXT_PERM_USER should have 'basic' permission, got: {perms}"
+
+    # --- SLACK_USER path ---
+    slack_email = "slack_perms_check@example.com"
+    slack_user = UserManager.create(email=slack_email)
+
+    slack_user = UserManager.set_role(
+        user_to_set=slack_user,
+        target_role=UserRole.SLACK_USER,
+        user_performing_action=admin_user,
+        explicit_override=True,
+    )
+
+    basic_emails = _get_default_group_member_emails(admin_user, "Basic")
+    assert slack_email not in basic_emails
+
+    upgraded = UserManager.create(email=slack_email)
+    assert upgraded.role == UserRole.BASIC
+
+    perms = UserManager.get_permissions(upgraded)
+    assert (
+        "basic" in perms
+    ), f"Upgraded SLACK_USER should have 'basic' permission, got: {perms}"

backend/tests/integration/tests/users/test_reactivation_groups.py

@@ -0,0 +1,54 @@
+"""Integration tests for default group reconciliation on user reactivation.
+
+Verifies that:
+- A deactivated user retains default group membership after reactivation
+- Reactivation via the admin API reconciles missing group membership
+"""
+
+from tests.integration.common_utils.managers.user import UserManager
+from tests.integration.common_utils.managers.user_group import UserGroupManager
+from tests.integration.common_utils.test_models import DATestUser
+
+
+def _get_default_group_member_emails(
+    admin_user: DATestUser,
+    group_name: str,
+) -> set[str]:
+    """Get the set of emails of all members in a named default group."""
+    all_groups = UserGroupManager.get_all(admin_user, include_default=True)
+    matched = [g for g in all_groups if g.is_default and g.name == group_name]
+    assert matched, f"Default group '{group_name}' not found"
+    return {u.email for u in matched[0].users}
+
+
+def test_reactivated_user_retains_default_group(
+    reset: None,  # noqa: ARG001
+) -> None:
+    """Deactivating and reactivating a user should preserve their
+    default group membership."""
+    admin_user: DATestUser = UserManager.create(name="admin_user")
+    basic_user: DATestUser = UserManager.create(name="basic_user")
+
+    # Verify user is in Basic group initially
+    basic_emails = _get_default_group_member_emails(admin_user, "Basic")
+    assert basic_user.email in basic_emails
+
+    # Deactivate the user
+    UserManager.set_status(
+        user_to_set=basic_user,
+        target_status=False,
+        user_performing_action=admin_user,
+    )
+
+    # Reactivate the user
+    UserManager.set_status(
+        user_to_set=basic_user,
+        target_status=True,
+        user_performing_action=admin_user,
+    )
+
+    # Verify user is still in Basic group after reactivation
+    basic_emails = _get_default_group_member_emails(admin_user, "Basic")
+    assert (
+        basic_user.email in basic_emails
+    ), "Reactivated user should still be in Basic default group"

backend/tests/unit/onyx/auth/test_permissions.py

@@ -0,0 +1,176 @@
+"""
+Unit tests for onyx.auth.permissions — pure logic and FastAPI dependency.
+"""
+
+from unittest.mock import MagicMock
+
+import pytest
+
+from onyx.auth.permissions import ALL_PERMISSIONS
+from onyx.auth.permissions import get_effective_permissions
+from onyx.auth.permissions import require_permission
+from onyx.auth.permissions import resolve_effective_permissions
+from onyx.db.enums import Permission
+from onyx.error_handling.error_codes import OnyxErrorCode
+from onyx.error_handling.exceptions import OnyxError
+
+
+# ---------------------------------------------------------------------------
+# resolve_effective_permissions
+# ---------------------------------------------------------------------------
+
+
+class TestResolveEffectivePermissions:
+    def test_empty_set(self) -> None:
+        assert resolve_effective_permissions(set()) == set()
+
+    def test_basic_no_implications(self) -> None:
+        result = resolve_effective_permissions({"basic"})
+        assert result == {"basic"}
+
+    def test_single_implication(self) -> None:
+        result = resolve_effective_permissions({"add:agents"})
+        assert result == {"add:agents", "read:agents"}
+
+    def test_manage_agents_implies_add_and_read(self) -> None:
+        """manage:agents directly maps to {add:agents, read:agents}."""
+        result = resolve_effective_permissions({"manage:agents"})
+        assert result == {"manage:agents", "add:agents", "read:agents"}
+
+    def test_manage_connectors_chain(self) -> None:
+        result = resolve_effective_permissions({"manage:connectors"})
+        assert result == {"manage:connectors", "add:connectors", "read:connectors"}
+
+    def test_manage_document_sets(self) -> None:
+        result = resolve_effective_permissions({"manage:document_sets"})
+        assert result == {
+            "manage:document_sets",
+            "read:document_sets",
+            "read:connectors",
+        }
+
+    def test_manage_user_groups_implies_all_reads(self) -> None:
+        result = resolve_effective_permissions({"manage:user_groups"})
+        assert result == {
+            "manage:user_groups",
+            "read:connectors",
+            "read:document_sets",
+            "read:agents",
+            "read:users",
+        }
+
+    def test_admin_override(self) -> None:
+        result = resolve_effective_permissions({"admin"})
+        assert result == set(ALL_PERMISSIONS)
+
+    def test_admin_with_others(self) -> None:
+        result = resolve_effective_permissions({"admin", "basic"})
+        assert result == set(ALL_PERMISSIONS)
+
+    def test_multi_group_union(self) -> None:
+        result = resolve_effective_permissions(
+            {"add:agents", "manage:connectors", "basic"}
+        )
+        assert result == {
+            "basic",
+            "add:agents",
+            "read:agents",
+            "manage:connectors",
+            "add:connectors",
+            "read:connectors",
+        }
+
+    def test_toggle_permission_no_implications(self) -> None:
+        result = resolve_effective_permissions({"read:agent_analytics"})
+        assert result == {"read:agent_analytics"}
+
+    def test_all_permissions_for_admin(self) -> None:
+        result = resolve_effective_permissions({"admin"})
+        assert len(result) == len(ALL_PERMISSIONS)
+
+
+# ---------------------------------------------------------------------------
+# get_effective_permissions (expands implied at read time)
+# ---------------------------------------------------------------------------
+
+
+class TestGetEffectivePermissions:
+    def test_expands_implied_permissions(self) -> None:
+        """Column stores only granted; get_effective_permissions expands implied."""
+        user = MagicMock()
+        user.effective_permissions = ["add:agents"]
+        result = get_effective_permissions(user)
+        assert result == {Permission.ADD_AGENTS, Permission.READ_AGENTS}
+
+    def test_admin_expands_to_all(self) -> None:
+        user = MagicMock()
+        user.effective_permissions = ["admin"]
+        result = get_effective_permissions(user)
+        assert result == set(Permission)
+
+    def test_basic_stays_basic(self) -> None:
+        user = MagicMock()
+        user.effective_permissions = ["basic"]
+        result = get_effective_permissions(user)
+        assert result == {Permission.BASIC_ACCESS}
+
+    def test_empty_column(self) -> None:
+        user = MagicMock()
+        user.effective_permissions = []
+        result = get_effective_permissions(user)
+        assert result == set()
+
+
+# ---------------------------------------------------------------------------
+# require_permission (FastAPI dependency)
+# ---------------------------------------------------------------------------
+
+
+class TestRequirePermission:
+    @pytest.mark.asyncio
+    async def test_admin_bypass(self) -> None:
+        """Admin stored in column should pass any permission check."""
+        user = MagicMock()
+        user.effective_permissions = ["admin"]
+
+        dep = require_permission(Permission.MANAGE_CONNECTORS)
+        result = await dep(user=user)
+        assert result is user
+
+    @pytest.mark.asyncio
+    async def test_has_required_permission(self) -> None:
+        user = MagicMock()
+        user.effective_permissions = ["manage:connectors"]
+
+        dep = require_permission(Permission.MANAGE_CONNECTORS)
+        result = await dep(user=user)
+        assert result is user
+
+    @pytest.mark.asyncio
+    async def test_implied_permission_passes(self) -> None:
+        """manage:connectors implies read:connectors at read time."""
+        user = MagicMock()
+        user.effective_permissions = ["manage:connectors"]
+
+        dep = require_permission(Permission.READ_CONNECTORS)
+        result = await dep(user=user)
+        assert result is user
+
+    @pytest.mark.asyncio
+    async def test_missing_permission_raises(self) -> None:
+        user = MagicMock()
+        user.effective_permissions = ["basic"]
+
+        dep = require_permission(Permission.MANAGE_CONNECTORS)
+        with pytest.raises(OnyxError) as exc_info:
+            await dep(user=user)
+        assert exc_info.value.error_code == OnyxErrorCode.INSUFFICIENT_PERMISSIONS
+
+    @pytest.mark.asyncio
+    async def test_empty_permissions_fails(self) -> None:
+        user = MagicMock()
+        user.effective_permissions = []
+
+        dep = require_permission(Permission.BASIC_ACCESS)
+        with pytest.raises(OnyxError):
+            await dep(user=user)

backend/tests/unit/onyx/auth/test_user_create_schema.py

@@ -0,0 +1,29 @@
+"""
+Unit tests for UserCreate schema dict methods.
+
+Verifies that account_type is always included in create_update_dict
+and create_update_dict_superuser.
+"""
+
+from onyx.auth.schemas import UserCreate
+from onyx.db.enums import AccountType
+
+
+def test_create_update_dict_includes_default_account_type() -> None:
+    uc = UserCreate(email="a@b.com", password="secret123")
+    d = uc.create_update_dict()
+    assert d["account_type"] == AccountType.STANDARD
+
+
+def test_create_update_dict_includes_explicit_account_type() -> None:
+    uc = UserCreate(
+        email="a@b.com", password="secret123", account_type=AccountType.SERVICE_ACCOUNT
+    )
+    d = uc.create_update_dict()
+    assert d["account_type"] == AccountType.STANDARD
+
+
+def test_create_update_dict_superuser_includes_account_type() -> None:
+    uc = UserCreate(email="a@b.com", password="secret123")
+    d = uc.create_update_dict_superuser()
+    assert d["account_type"] == AccountType.STANDARD

backend/tests/unit/onyx/chat/test_multi_model_streaming.py

@@ -0,0 +1,754 @@
+"""Unit tests for multi-model streaming validation and DB helpers.
+
+These are pure unit tests — no real database or LLM calls required.
+The validation logic in handle_multi_model_stream fires before any external
+calls, so we can trigger it with lightweight mocks.
+"""
+
+import time
+from collections.abc import Generator
+from typing import Any
+from typing import cast
+from unittest.mock import MagicMock
+from unittest.mock import patch
+from uuid import uuid4
+
+import pytest
+
+from onyx.chat.models import StreamingError
+from onyx.configs.constants import MessageType
+from onyx.db.chat import set_preferred_response
+from onyx.llm.override_models import LLMOverride
+from onyx.server.query_and_chat.models import SendMessageRequest
+from onyx.server.query_and_chat.placement import Placement
+from onyx.server.query_and_chat.streaming_models import OverallStop
+from onyx.server.query_and_chat.streaming_models import Packet
+from onyx.server.query_and_chat.streaming_models import ReasoningStart
+from onyx.utils.variable_functionality import global_version
+
+
+@pytest.fixture(autouse=True)
+def _restore_ee_version() -> Generator[None, None, None]:
+    """Reset EE global state after each test.
+
+    Importing onyx.chat.process_message triggers set_is_ee_based_on_env_variable()
+    (via the celery client import chain).  Without this fixture, the EE flag stays
+    True for the rest of the session and breaks unrelated tests that mock Confluence
+    or other connectors and assume EE is disabled.
+    """
+    original = global_version._is_ee
+    yield
+    global_version._is_ee = original
+
+
+# ---------------------------------------------------------------------------
+# Helpers
+# ---------------------------------------------------------------------------
+
+
+def _make_request(**kwargs: Any) -> SendMessageRequest:
+    defaults: dict[str, Any] = {
+        "message": "hello",
+        "chat_session_id": uuid4(),
+    }
+    defaults.update(kwargs)
+    return SendMessageRequest(**defaults)
+
+
+def _make_override(provider: str = "openai", version: str = "gpt-4") -> LLMOverride:
+    return LLMOverride(model_provider=provider, model_version=version)
+
+
+def _first_from_stream(req: SendMessageRequest, overrides: list[LLMOverride]) -> Any:
+    """Return the first item yielded by handle_multi_model_stream."""
+    from onyx.chat.process_message import handle_multi_model_stream
+
+    user = MagicMock()
+    user.is_anonymous = False
+    user.email = "test@example.com"
+    db = MagicMock()
+
+    gen = handle_multi_model_stream(req, user, db, overrides)
+    return next(gen)
+
+
+# ---------------------------------------------------------------------------
+# handle_multi_model_stream — validation
+# ---------------------------------------------------------------------------
+
+
+class TestRunMultiModelStreamValidation:
+    def test_single_override_yields_error(self) -> None:
+        """Exactly 1 override is not multi-model — yields StreamingError."""
+        req = _make_request()
+        result = _first_from_stream(req, [_make_override()])
+        assert isinstance(result, StreamingError)
+        assert "2-3" in result.error
+
+    def test_four_overrides_yields_error(self) -> None:
+        """4 overrides exceeds maximum — yields StreamingError."""
+        req = _make_request()
+        result = _first_from_stream(
+            req,
+            [
+                _make_override("openai", "gpt-4"),
+                _make_override("anthropic", "claude-3"),
+                _make_override("google", "gemini-pro"),
+                _make_override("cohere", "command-r"),
+            ],
+        )
+        assert isinstance(result, StreamingError)
+        assert "2-3" in result.error
+
+    def test_zero_overrides_yields_error(self) -> None:
+        """Empty override list yields StreamingError."""
+        req = _make_request()
+        result = _first_from_stream(req, [])
+        assert isinstance(result, StreamingError)
+        assert "2-3" in result.error
+
+    def test_deep_research_yields_error(self) -> None:
+        """deep_research=True is incompatible with multi-model — yields StreamingError."""
+        req = _make_request(deep_research=True)
+        result = _first_from_stream(
+            req, [_make_override(), _make_override("anthropic", "claude-3")]
+        )
+        assert isinstance(result, StreamingError)
+        assert "not supported" in result.error
+
+    def test_exactly_two_overrides_is_minimum(self) -> None:
+        """Boundary: 1 override yields error, 2 overrides passes validation."""
+        req = _make_request()
+        # 1 override must yield a StreamingError
+        result = _first_from_stream(req, [_make_override()])
+        assert isinstance(
+            result, StreamingError
+        ), "1 override should yield StreamingError"
+        # 2 overrides must NOT yield a validation StreamingError (may raise later due to
+        # missing session, that's OK — validation itself passed)
+        try:
+            result2 = _first_from_stream(
+                req, [_make_override(), _make_override("anthropic", "claude-3")]
+            )
+            if isinstance(result2, StreamingError) and "2-3" in result2.error:
+                pytest.fail(
+                    f"2 overrides should pass validation, got StreamingError: {result2.error}"
+                )
+        except Exception:
+            pass  # Any non-validation error means validation passed
+
+
+# ---------------------------------------------------------------------------
+# set_preferred_response — validation (mocked db)
+# ---------------------------------------------------------------------------
+
+
+class TestSetPreferredResponseValidation:
+    def test_user_message_not_found(self) -> None:
+        db = MagicMock()
+        db.get.return_value = None
+
+        with pytest.raises(ValueError, match="not found"):
+            set_preferred_response(
+                db, user_message_id=999, preferred_assistant_message_id=1
+            )
+
+    def test_wrong_message_type(self) -> None:
+        """Cannot set preferred response on a non-USER message."""
+        db = MagicMock()
+        user_msg = MagicMock()
+        user_msg.message_type = MessageType.ASSISTANT  # wrong type
+
+        db.get.return_value = user_msg
+
+        with pytest.raises(ValueError, match="not a user message"):
+            set_preferred_response(
+                db, user_message_id=1, preferred_assistant_message_id=2
+            )
+
+    def test_assistant_message_not_found(self) -> None:
+        db = MagicMock()
+        user_msg = MagicMock()
+        user_msg.message_type = MessageType.USER
+
+        # First call returns user_msg, second call (for assistant) returns None
+        db.get.side_effect = [user_msg, None]
+
+        with pytest.raises(ValueError, match="not found"):
+            set_preferred_response(
+                db, user_message_id=1, preferred_assistant_message_id=2
+            )
+
+    def test_assistant_not_child_of_user(self) -> None:
+        db = MagicMock()
+        user_msg = MagicMock()
+        user_msg.message_type = MessageType.USER
+
+        assistant_msg = MagicMock()
+        assistant_msg.parent_message_id = 999  # different parent
+
+        db.get.side_effect = [user_msg, assistant_msg]
+
+        with pytest.raises(ValueError, match="not a child"):
+            set_preferred_response(
+                db, user_message_id=1, preferred_assistant_message_id=2
+            )
+
+    def test_valid_call_sets_preferred_response_id(self) -> None:
+        db = MagicMock()
+        user_msg = MagicMock()
+        user_msg.message_type = MessageType.USER
+
+        assistant_msg = MagicMock()
+        assistant_msg.parent_message_id = 1  # correct parent
+
+        db.get.side_effect = [user_msg, assistant_msg]
+
+        set_preferred_response(db, user_message_id=1, preferred_assistant_message_id=2)
+
+        assert user_msg.preferred_response_id == 2
+        assert user_msg.latest_child_message_id == 2
+
+
+# ---------------------------------------------------------------------------
+# LLMOverride — display_name field
+# ---------------------------------------------------------------------------
+
+
+class TestLLMOverrideDisplayName:
+    def test_display_name_defaults_none(self) -> None:
+        override = LLMOverride(model_provider="openai", model_version="gpt-4")
+        assert override.display_name is None
+
+    def test_display_name_set(self) -> None:
+        override = LLMOverride(
+            model_provider="openai",
+            model_version="gpt-4",
+            display_name="GPT-4 Turbo",
+        )
+        assert override.display_name == "GPT-4 Turbo"
+
+    def test_display_name_serializes(self) -> None:
+        override = LLMOverride(
+            model_provider="anthropic",
+            model_version="claude-opus-4-6",
+            display_name="Claude Opus",
+        )
+        d = override.model_dump()
+        assert d["display_name"] == "Claude Opus"
+
+
+# ---------------------------------------------------------------------------
+# _run_models — drain loop behaviour
+# ---------------------------------------------------------------------------
+
+
+def _make_setup(n_models: int = 1) -> MagicMock:
+    """Minimal ChatTurnSetup mock whose fields pass Pydantic validation in _run_model."""
+    setup = MagicMock()
+    setup.llms = [MagicMock() for _ in range(n_models)]
+    setup.model_display_names = [f"model-{i}" for i in range(n_models)]
+    setup.check_is_connected = MagicMock(return_value=True)
+    setup.reserved_messages = [MagicMock() for _ in range(n_models)]
+    setup.reserved_token_count = 100
+    # Fields consumed by SearchToolConfig / CustomToolConfig / FileReaderToolConfig
+    # constructors inside _run_model — must be typed correctly for Pydantic.
+    setup.new_msg_req.deep_research = False
+    setup.new_msg_req.internal_search_filters = None
+    setup.new_msg_req.allowed_tool_ids = None
+    setup.new_msg_req.include_citations = True
+    setup.search_params.project_id_filter = None
+    setup.search_params.persona_id_filter = None
+    setup.bypass_acl = False
+    setup.slack_context = None
+    setup.available_files.user_file_ids = []
+    setup.available_files.chat_file_ids = []
+    setup.forced_tool_id = None
+    setup.simple_chat_history = []
+    setup.chat_session.id = uuid4()
+    setup.user_message.id = None
+    setup.custom_tool_additional_headers = None
+    setup.mcp_headers = None
+    return setup
+
+
+def _run_models_collect(setup: MagicMock) -> list:
+    """Drive _run_models to completion and return all yielded items."""
+    from onyx.chat.process_message import _run_models
+
+    return list(_run_models(setup, MagicMock(), MagicMock()))
+
+
+class TestRunModels:
+    """Tests for the _run_models worker-thread drain loop.
+
+    All external dependencies (LLM, DB, tools) are patched out.  Worker threads
+    still run but return immediately since run_llm_loop is mocked.
+    """
+
+    def test_n1_overall_stop_from_llm_loop_passes_through(self) -> None:
+        """OverallStop emitted by run_llm_loop is passed through the drain loop unchanged."""
+
+        def emit_stop(**kwargs: Any) -> None:
+            kwargs["emitter"].emit(
+                Packet(
+                    placement=Placement(turn_index=0),
+                    obj=OverallStop(stop_reason="complete"),
+                )
+            )
+
+        with (
+            patch("onyx.chat.process_message.run_llm_loop", side_effect=emit_stop),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch("onyx.chat.process_message.llm_loop_completion_handle"),
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            packets = _run_models_collect(_make_setup(n_models=1))
+
+        stops = [
+            p
+            for p in packets
+            if isinstance(p, Packet) and isinstance(p.obj, OverallStop)
+        ]
+        assert len(stops) == 1
+        stop_obj = stops[0].obj
+        assert isinstance(stop_obj, OverallStop)
+        assert stop_obj.stop_reason == "complete"
+
+    def test_n1_emitted_packet_has_model_index_zero(self) -> None:
+        """Single-model path: model_index is 0 (Emitter defaults model_idx=0)."""
+
+        def emit_one(**kwargs: Any) -> None:
+            kwargs["emitter"].emit(
+                Packet(placement=Placement(turn_index=0), obj=ReasoningStart())
+            )
+
+        with (
+            patch("onyx.chat.process_message.run_llm_loop", side_effect=emit_one),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch("onyx.chat.process_message.llm_loop_completion_handle"),
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            packets = _run_models_collect(_make_setup(n_models=1))
+
+        reasoning = [
+            p
+            for p in packets
+            if isinstance(p, Packet) and isinstance(p.obj, ReasoningStart)
+        ]
+        assert len(reasoning) == 1
+        assert reasoning[0].placement.model_index == 0
+
+    def test_n2_each_model_packet_tagged_with_its_index(self) -> None:
+        """Multi-model path: packets from model 0 get index=0, model 1 gets index=1."""
+
+        def emit_one(**kwargs: Any) -> None:
+            # _model_idx is set by _run_model based on position in setup.llms
+            emitter = kwargs["emitter"]
+            emitter.emit(
+                Packet(placement=Placement(turn_index=0), obj=ReasoningStart())
+            )
+
+        with (
+            patch("onyx.chat.process_message.run_llm_loop", side_effect=emit_one),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch("onyx.chat.process_message.llm_loop_completion_handle"),
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            packets = _run_models_collect(_make_setup(n_models=2))
+
+        reasoning = [
+            p
+            for p in packets
+            if isinstance(p, Packet) and isinstance(p.obj, ReasoningStart)
+        ]
+        assert len(reasoning) == 2
+        indices = {p.placement.model_index for p in reasoning}
+        assert indices == {0, 1}
+
+    def test_model_error_yields_streaming_error(self) -> None:
+        """An exception inside a worker thread is surfaced as a StreamingError."""
+
+        def always_fail(**_kwargs: Any) -> None:
+            raise RuntimeError("intentional test failure")
+
+        with (
+            patch("onyx.chat.process_message.run_llm_loop", side_effect=always_fail),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch("onyx.chat.process_message.llm_loop_completion_handle"),
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            packets = _run_models_collect(_make_setup(n_models=1))
+
+        errors = [p for p in packets if isinstance(p, StreamingError)]
+        assert len(errors) == 1
+        assert errors[0].error_code == "MODEL_ERROR"
+        assert "intentional test failure" in errors[0].error
+
+    def test_one_model_error_does_not_stop_other_models(self) -> None:
+        """A failing model yields StreamingError; the surviving model's packets still arrive."""
+        setup = _make_setup(n_models=2)
+
+        def fail_model_0_succeed_model_1(**kwargs: Any) -> None:
+            if kwargs["llm"] is setup.llms[0]:
+                raise RuntimeError("model 0 failed")
+            kwargs["emitter"].emit(
+                Packet(placement=Placement(turn_index=0), obj=ReasoningStart())
+            )
+
+        with (
+            patch(
+                "onyx.chat.process_message.run_llm_loop",
+                side_effect=fail_model_0_succeed_model_1,
+            ),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch("onyx.chat.process_message.llm_loop_completion_handle"),
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            packets = _run_models_collect(setup)
+
+        errors = [p for p in packets if isinstance(p, StreamingError)]
+        assert len(errors) == 1
+
+        reasoning = [
+            p
+            for p in packets
+            if isinstance(p, Packet) and isinstance(p.obj, ReasoningStart)
+        ]
+        assert len(reasoning) == 1
+        assert reasoning[0].placement.model_index == 1
+
+    def test_cancellation_yields_user_cancelled_stop(self) -> None:
+        """If check_is_connected returns False, drain loop emits user_cancelled."""
+
+        def slow_llm(**_kwargs: Any) -> None:
+            time.sleep(0.3)  # Outlasts the 50 ms queue-poll interval
+
+        setup = _make_setup(n_models=1)
+        setup.check_is_connected = MagicMock(return_value=False)
+
+        with (
+            patch("onyx.chat.process_message.run_llm_loop", side_effect=slow_llm),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch("onyx.chat.process_message.llm_loop_completion_handle"),
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            packets = _run_models_collect(setup)
+
+        stops = [
+            p
+            for p in packets
+            if isinstance(p, Packet) and isinstance(p.obj, OverallStop)
+        ]
+        assert any(
+            isinstance(s.obj, OverallStop) and s.obj.stop_reason == "user_cancelled"
+            for s in stops
+        )
+
+    def test_stop_button_calls_completion_for_all_models(self) -> None:
+        """llm_loop_completion_handle must be called for all models when the stop button fires.
+
+        Regression test for the disconnect-cleanup bug: the old
+        run_chat_loop_with_state_containers always called completion_callback in
+        its finally block (even on disconnect) so the DB message was updated from
+        the TERMINATED placeholder to a partial answer.  The new _run_models must
+        replicate this — otherwise the integration test
+        test_send_message_disconnect_and_cleanup fails because the message stays
+        as "Response was terminated prior to completion, try regenerating."
+        """
+
+        def slow_llm(**_kwargs: Any) -> None:
+            time.sleep(0.3)
+
+        setup = _make_setup(n_models=2)
+        setup.check_is_connected = MagicMock(return_value=False)
+
+        with (
+            patch("onyx.chat.process_message.run_llm_loop", side_effect=slow_llm),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch(
+                "onyx.chat.process_message.llm_loop_completion_handle"
+            ) as mock_handle,
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            _run_models_collect(setup)
+
+        # Must be called once per model, not zero times
+        assert mock_handle.call_count == 2
+
+    def test_completion_handle_called_for_each_successful_model(self) -> None:
+        """llm_loop_completion_handle must be called once per model that succeeded."""
+        setup = _make_setup(n_models=2)
+
+        with (
+            patch("onyx.chat.process_message.run_llm_loop"),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch(
+                "onyx.chat.process_message.llm_loop_completion_handle"
+            ) as mock_handle,
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            _run_models_collect(setup)
+
+        assert mock_handle.call_count == 2
+
+    def test_completion_handle_not_called_for_failed_model(self) -> None:
+        """llm_loop_completion_handle must be skipped for a model that raised."""
+
+        def always_fail(**_kwargs: Any) -> None:
+            raise RuntimeError("fail")
+
+        with (
+            patch("onyx.chat.process_message.run_llm_loop", side_effect=always_fail),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch(
+                "onyx.chat.process_message.llm_loop_completion_handle"
+            ) as mock_handle,
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            _run_models_collect(_make_setup(n_models=1))
+
+        mock_handle.assert_not_called()
+
+    def test_http_disconnect_completion_via_generator_exit(self) -> None:
+        """GeneratorExit from HTTP disconnect triggers main-thread completion.
+
+        When the HTTP client closes the connection, Starlette throws GeneratorExit
+        into the stream generator. The finally block sets drain_done (signalling
+        emitters to stop blocking), waits for workers via executor.shutdown(wait=True),
+        then calls llm_loop_completion_handle for each successful model from the main
+        thread.
+
+        This is the primary regression for test_send_message_disconnect_and_cleanup:
+        the integration test disconnects mid-stream and expects the DB message to be
+        updated from the TERMINATED placeholder to the real response.
+        """
+        import threading
+
+        completion_called = threading.Event()
+
+        def emit_then_block_until_drain(**kwargs: Any) -> None:
+            """Emit one packet (to give the drain loop a yield point), then block
+            until drain_done is set — simulating a mid-stream LLM call that exits
+            promptly once the emitter signals shutdown.
+            """
+            emitter = kwargs["emitter"]
+            emitter.emit(
+                Packet(placement=Placement(turn_index=0), obj=ReasoningStart())
+            )
+            # Block until drain_done is set by gen.close(). The Emitter's _drain_done
+            # is the same Event that _run_models sets, so this unblocks promptly.
+            emitter._drain_done.wait(timeout=5)
+
+        setup = _make_setup(n_models=1)
+        # is_connected() always True — HTTP disconnect does NOT set the Redis stop fence.
+        setup.check_is_connected = MagicMock(return_value=True)
+
+        with (
+            patch(
+                "onyx.chat.process_message.run_llm_loop",
+                side_effect=emit_then_block_until_drain,
+            ),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch(
+                "onyx.chat.process_message.llm_loop_completion_handle",
+                side_effect=lambda *_, **__: completion_called.set(),
+            ) as mock_handle,
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            from onyx.chat.process_message import _run_models
+
+            gen = cast(Generator, _run_models(setup, MagicMock(), MagicMock()))
+            first = next(gen)
+            assert isinstance(first, Packet)
+            # Simulate Starlette closing the stream on HTTP client disconnect.
+            # gen.close() → GeneratorExit → finally → drain_done.set() →
+            # executor.shutdown(wait=True) → main thread completes models.
+            gen.close()
+
+            assert (
+                completion_called.is_set()
+            ), "main thread must call completion for the successful model"
+            assert mock_handle.call_count == 1
+
+    def test_b1_race_disconnect_handler_completes_already_finished_model(self) -> None:
+        """B1 regression: model finishes BEFORE GeneratorExit fires.
+
+        The worker exits _run_model before drain_done is set. When gen.close()
+        fires afterward, the finally block sets drain_done, waits for workers
+        (already done), then the main thread calls llm_loop_completion_handle.
+
+        Contrast with test_http_disconnect_completion_via_generator_exit, which
+        tests the opposite ordering (worker finishes AFTER disconnect).
+        """
+        import threading
+        import time
+
+        completion_called = threading.Event()
+
+        def emit_and_return_immediately(**kwargs: Any) -> None:
+            # Emit one packet so the drain loop has something to yield, then return
+            # immediately — no blocking.  The worker will be done in microseconds.
+            kwargs["emitter"].emit(
+                Packet(placement=Placement(turn_index=0), obj=ReasoningStart())
+            )
+
+        setup = _make_setup(n_models=1)
+        setup.check_is_connected = MagicMock(return_value=True)
+
+        with (
+            patch(
+                "onyx.chat.process_message.run_llm_loop",
+                side_effect=emit_and_return_immediately,
+            ),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch(
+                "onyx.chat.process_message.llm_loop_completion_handle",
+                side_effect=lambda *_, **__: completion_called.set(),
+            ) as mock_handle,
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            from onyx.chat.process_message import _run_models
+
+            gen = cast(Generator, _run_models(setup, MagicMock(), MagicMock()))
+            first = next(gen)
+            assert isinstance(first, Packet)
+
+            # Give the worker thread time to finish completely (emit + return +
+            # finally + self-completion check).  It does almost no work, so 100 ms
+            # is far more than enough while still keeping the test fast.
+            time.sleep(0.1)
+
+            # Now close — worker is already done, so else-branch handles completion.
+            gen.close()
+
+            assert completion_called.wait(
+                timeout=5
+            ), "disconnect handler must call completion for a model that already finished"
+            assert mock_handle.call_count == 1, "completion must be called exactly once"
+
+    def test_stop_button_does_not_call_completion_for_errored_model(self) -> None:
+        """B2 regression: stop-button must NOT call completion for an errored model.
+
+        When model 0 raises an exception, its reserved ChatMessage must not be
+        saved with 'stopped by user' — that message is wrong for a model that
+        errored.  llm_loop_completion_handle must only be called for non-errored
+        models when the stop button fires.
+        """
+
+        def fail_model_0(**kwargs: Any) -> None:
+            if kwargs["llm"] is setup.llms[0]:
+                raise RuntimeError("model 0 errored")
+            # Model 1: run forever (stop button fires before it finishes)
+            time.sleep(10)
+
+        setup = _make_setup(n_models=2)
+        # Return False immediately so the stop-button path fires while model 1
+        # is still sleeping (model 0 has already errored by then).
+        setup.check_is_connected = lambda: False
+
+        with (
+            patch("onyx.chat.process_message.run_llm_loop", side_effect=fail_model_0),
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch(
+                "onyx.chat.process_message.llm_loop_completion_handle"
+            ) as mock_handle,
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            _run_models_collect(setup)
+
+        # Completion must NOT be called for model 0 (it errored).
+        # It MAY be called for model 1 (still in-flight when stop fired).
+        for call in mock_handle.call_args_list:
+            assert (
+                call.kwargs.get("llm") is not setup.llms[0]
+            ), "llm_loop_completion_handle must not be called for the errored model"
+
+    def test_external_state_container_used_for_model_zero(self) -> None:
+        """When provided, external_state_container is used as state_containers[0]."""
+        from onyx.chat.chat_state import ChatStateContainer
+        from onyx.chat.process_message import _run_models
+
+        external = ChatStateContainer()
+        setup = _make_setup(n_models=1)
+
+        with (
+            patch("onyx.chat.process_message.run_llm_loop") as mock_llm,
+            patch("onyx.chat.process_message.run_deep_research_llm_loop"),
+            patch("onyx.chat.process_message.construct_tools", return_value={}),
+            patch("onyx.chat.process_message.get_session_with_current_tenant"),
+            patch("onyx.chat.process_message.llm_loop_completion_handle"),
+            patch(
+                "onyx.chat.process_message.get_llm_token_counter",
+                return_value=lambda _: 0,
+            ),
+        ):
+            list(
+                _run_models(
+                    setup, MagicMock(), MagicMock(), external_state_container=external
+                )
+            )
+
+        # The state_container kwarg passed to run_llm_loop must be the external one
+        call_kwargs = mock_llm.call_args.kwargs
+        assert call_kwargs["state_container"] is external

backend/tests/unit/onyx/db/test_assign_default_groups.py

@@ -0,0 +1,176 @@
+"""
+Unit tests for assign_user_to_default_groups__no_commit in onyx.db.users.
+
+Covers:
+1. Standard/service-account users get assigned to the correct default group
+2. BOT, EXT_PERM_USER, ANONYMOUS account types are skipped
+3. Missing default group raises RuntimeError
+4. Already-in-group is a no-op
+5. IntegrityError race condition is handled gracefully
+6. The function never commits the session
+"""
+
+from unittest.mock import MagicMock
+from uuid import uuid4
+
+import pytest
+from sqlalchemy.exc import IntegrityError
+
+from onyx.db.enums import AccountType
+from onyx.db.models import User__UserGroup
+from onyx.db.models import UserGroup
+from onyx.db.users import assign_user_to_default_groups__no_commit
+
+
+def _mock_user(
+    account_type: AccountType = AccountType.STANDARD,
+    email: str = "test@example.com",
+) -> MagicMock:
+    user = MagicMock()
+    user.id = uuid4()
+    user.email = email
+    user.account_type = account_type
+    return user
+
+
+def _mock_group(name: str = "Basic", group_id: int = 1) -> MagicMock:
+    group = MagicMock()
+    group.id = group_id
+    group.name = name
+    group.is_default = True
+    return group
+
+
+def _make_query_chain(first_return: object = None) -> MagicMock:
+    """Returns a mock that supports .filter(...).filter(...).first() chaining."""
+    chain = MagicMock()
+    chain.filter.return_value = chain
+    chain.first.return_value = first_return
+    return chain
+
+
+def _setup_db_session(
+    group_result: object = None,
+    membership_result: object = None,
+) -> MagicMock:
+    """Create a db_session mock that routes query(UserGroup) and query(User__UserGroup)."""
+    db_session = MagicMock()
+
+    group_chain = _make_query_chain(group_result)
+    membership_chain = _make_query_chain(membership_result)
+
+    def query_side_effect(model: type) -> MagicMock:
+        if model is UserGroup:
+            return group_chain
+        if model is User__UserGroup:
+            return membership_chain
+        return MagicMock()
+
+    db_session.query.side_effect = query_side_effect
+    return db_session
+
+
+def test_standard_user_assigned_to_basic_group() -> None:
+    group = _mock_group("Basic")
+    db_session = _setup_db_session(group_result=group, membership_result=None)
+    savepoint = MagicMock()
+    db_session.begin_nested.return_value = savepoint
+    user = _mock_user(AccountType.STANDARD)
+
+    assign_user_to_default_groups__no_commit(db_session, user, is_admin=False)
+
+    db_session.add.assert_called_once()
+    added = db_session.add.call_args[0][0]
+    assert isinstance(added, User__UserGroup)
+    assert added.user_id == user.id
+    assert added.user_group_id == group.id
+    db_session.flush.assert_called_once()
+
+
+def test_admin_user_assigned_to_admin_group() -> None:
+    group = _mock_group("Admin", group_id=2)
+    db_session = _setup_db_session(group_result=group, membership_result=None)
+    savepoint = MagicMock()
+    db_session.begin_nested.return_value = savepoint
+    user = _mock_user(AccountType.STANDARD)
+
+    assign_user_to_default_groups__no_commit(db_session, user, is_admin=True)
+
+    db_session.add.assert_called_once()
+    added = db_session.add.call_args[0][0]
+    assert isinstance(added, User__UserGroup)
+    assert added.user_group_id == group.id
+
+
+@pytest.mark.parametrize(
+    "account_type",
+    [AccountType.BOT, AccountType.EXT_PERM_USER, AccountType.ANONYMOUS],
+)
+def test_excluded_account_types_skipped(account_type: AccountType) -> None:
+    db_session = MagicMock()
+    user = _mock_user(account_type)
+
+    assign_user_to_default_groups__no_commit(db_session, user)
+
+    db_session.query.assert_not_called()
+    db_session.add.assert_not_called()
+
+
+def test_service_account_not_skipped() -> None:
+    group = _mock_group("Basic")
+    db_session = _setup_db_session(group_result=group, membership_result=None)
+    savepoint = MagicMock()
+    db_session.begin_nested.return_value = savepoint
+    user = _mock_user(AccountType.SERVICE_ACCOUNT)
+
+    assign_user_to_default_groups__no_commit(db_session, user, is_admin=False)
+
+    db_session.add.assert_called_once()
+
+
+def test_missing_default_group_raises_error() -> None:
+    db_session = _setup_db_session(group_result=None)
+    user = _mock_user()
+
+    with pytest.raises(RuntimeError, match="Default group .* not found"):
+        assign_user_to_default_groups__no_commit(db_session, user)
+
+
+def test_already_in_group_is_noop() -> None:
+    group = _mock_group("Basic")
+    existing_membership = MagicMock()
+    db_session = _setup_db_session(
+        group_result=group, membership_result=existing_membership
+    )
+    user = _mock_user()
+
+    assign_user_to_default_groups__no_commit(db_session, user)
+
+    db_session.add.assert_not_called()
+    db_session.begin_nested.assert_not_called()
+
+
+def test_integrity_error_race_condition_handled() -> None:
+    group = _mock_group("Basic")
+    db_session = _setup_db_session(group_result=group, membership_result=None)
+    savepoint = MagicMock()
+    db_session.begin_nested.return_value = savepoint
+    db_session.flush.side_effect = IntegrityError(None, None, Exception("duplicate"))
+    user = _mock_user()
+
+    # Should not raise
+    assign_user_to_default_groups__no_commit(db_session, user)
+
+    savepoint.rollback.assert_called_once()
+
+
+def test_no_commit_called_on_successful_assignment() -> None:
+    group = _mock_group("Basic")
+    db_session = _setup_db_session(group_result=group, membership_result=None)
+    savepoint = MagicMock()
+    db_session.begin_nested.return_value = savepoint
+    user = _mock_user()
+
+    assign_user_to_default_groups__no_commit(db_session, user)
+
+    db_session.commit.assert_not_called()

backend/tests/unit/onyx/server/scim/conftest.py

@@ -113,6 +113,7 @@ def make_db_group(**kwargs: Any) -> MagicMock:
     group.name = kwargs.get("name", "Engineering")
     group.is_up_for_deletion = kwargs.get("is_up_for_deletion", False)
     group.is_up_to_date = kwargs.get("is_up_to_date", True)
+    group.is_default = kwargs.get("is_default", False)
     return group
 
 

backend/tests/unit/onyx/server/test_full_user_snapshot.py

@@ -3,6 +3,7 @@ from unittest.mock import MagicMock
 from uuid import uuid4
 
 from onyx.auth.schemas import UserRole
+from onyx.db.enums import AccountType
 from onyx.server.models import FullUserSnapshot
 from onyx.server.models import UserGroupInfo
 
@@ -25,6 +26,7 @@ def _mock_user(
     user.updated_at = updated_at or datetime.datetime(
         2025, 6, 15, tzinfo=datetime.timezone.utc
     )
+    user.account_type = AccountType.STANDARD
     return user
 
 

cli/cmd/agents.go

@@ -7,6 +7,7 @@ import (
 
 	"github.com/onyx-dot-app/onyx/cli/internal/api"
 	"github.com/onyx-dot-app/onyx/cli/internal/config"
+	"github.com/onyx-dot-app/onyx/cli/internal/exitcodes"
 	"github.com/spf13/cobra"
 )
 
@@ -16,16 +17,23 @@ func newAgentsCmd() *cobra.Command {
 	cmd := &cobra.Command{
 		Use:   "agents",
 		Short: "List available agents",
+		Long: `List all visible agents configured on the Onyx server.
+
+By default, output is a human-readable table with ID, name, and description.
+Use --json for machine-readable output.`,
+		Example: `  onyx-cli agents
+  onyx-cli agents --json
+  onyx-cli agents --json | jq '.[].name'`,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			cfg := config.Load()
 			if !cfg.IsConfigured() {
-				return fmt.Errorf("onyx CLI is not configured — run 'onyx-cli configure' first")
+				return exitcodes.New(exitcodes.NotConfigured, "onyx CLI is not configured\n  Run: onyx-cli configure")
 			}
 
 			client := api.NewClient(cfg)
 			agents, err := client.ListAgents(cmd.Context())
 			if err != nil {
-				return fmt.Errorf("failed to list agents: %w", err)
+				return fmt.Errorf("failed to list agents: %w\n  Check your connection with: onyx-cli validate-config", err)
 			}
 
 			if agentsJSON {

cli/cmd/ask.go

@@ -4,33 +4,65 @@ import (
 	"context"
 	"encoding/json"
 	"fmt"
+	"io"
 	"os"
 	"os/signal"
+	"strings"
 	"syscall"
 
 	"github.com/onyx-dot-app/onyx/cli/internal/api"
 	"github.com/onyx-dot-app/onyx/cli/internal/config"
+	"github.com/onyx-dot-app/onyx/cli/internal/exitcodes"
 	"github.com/onyx-dot-app/onyx/cli/internal/models"
+	"github.com/onyx-dot-app/onyx/cli/internal/overflow"
 	"github.com/spf13/cobra"
+	"golang.org/x/term"
 )
 
+const defaultMaxOutputBytes = 4096
+
 func newAskCmd() *cobra.Command {
 	var (
 		askAgentID int
 		askJSON    bool
+		askQuiet   bool
+		askPrompt  string
+		maxOutput  int
 	)
 
 	cmd := &cobra.Command{
 		Use:   "ask [question]",
 		Short: "Ask a one-shot question (non-interactive)",
-		Args:  cobra.ExactArgs(1),
+		Long: `Send a one-shot question to an Onyx agent and print the response.
+
+The question can be provided as a positional argument, via --prompt, or piped
+through stdin. When stdin contains piped data, it is sent as context along
+with the question from --prompt (or used as the question itself).
+
+When stdout is not a TTY (e.g., called by a script or AI agent), output is
+automatically truncated to --max-output bytes and the full response is saved
+to a temp file. Set --max-output 0 to disable truncation.`,
+		Args: cobra.MaximumNArgs(1),
+		Example: `  onyx-cli ask "What connectors are available?"
+  onyx-cli ask --agent-id 3 "Summarize our Q4 revenue"
+  onyx-cli ask --json "List all users" | jq '.event.content'
+  cat error.log | onyx-cli ask --prompt "Find the root cause"
+  echo "what is onyx?" | onyx-cli ask`,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			cfg := config.Load()
 			if !cfg.IsConfigured() {
-				return fmt.Errorf("onyx CLI is not configured — run 'onyx-cli configure' first")
+				return exitcodes.New(exitcodes.NotConfigured, "onyx CLI is not configured\n  Run: onyx-cli configure")
+			}
+
+			if askJSON && askQuiet {
+				return exitcodes.New(exitcodes.BadRequest, "--json and --quiet cannot be used together")
+			}
+
+			question, err := resolveQuestion(args, askPrompt)
+			if err != nil {
+				return err
 			}
 
-			question := args[0]
 			agentID := cfg.DefaultAgentID
 			if cmd.Flags().Changed("agent-id") {
 				agentID = askAgentID
@@ -50,9 +82,23 @@ func newAskCmd() *cobra.Command {
 				nil,
 			)
 
+			// Determine truncation threshold.
+			isTTY := term.IsTerminal(int(os.Stdout.Fd()))
+			truncateAt := 0 // 0 means no truncation
+			if cmd.Flags().Changed("max-output") {
+				truncateAt = maxOutput
+			} else if !isTTY {
+				truncateAt = defaultMaxOutputBytes
+			}
+
 			var sessionID string
 			var lastErr error
 			gotStop := false
+
+			// Overflow writer: tees to stdout and optionally to a temp file.
+			// In quiet mode, buffer everything and print once at the end.
+			ow := &overflow.Writer{Limit: truncateAt, Quiet: askQuiet}
+
 			for event := range ch {
 				if e, ok := event.(models.SessionCreatedEvent); ok {
 					sessionID = e.ChatSessionID
@@ -82,22 +128,50 @@ func newAskCmd() *cobra.Command {
 
 				switch e := event.(type) {
 				case models.MessageDeltaEvent:
-					fmt.Print(e.Content)
+					ow.Write(e.Content)
+				case models.SearchStartEvent:
+					if isTTY && !askQuiet {
+						if e.IsInternetSearch {
+							fmt.Fprintf(os.Stderr, "\033[2mSearching the web...\033[0m\n")
+						} else {
+							fmt.Fprintf(os.Stderr, "\033[2mSearching documents...\033[0m\n")
+						}
+					}
+				case models.SearchQueriesEvent:
+					if isTTY && !askQuiet {
+						for _, q := range e.Queries {
+							fmt.Fprintf(os.Stderr, "\033[2m  → %s\033[0m\n", q)
+						}
+					}
+				case models.SearchDocumentsEvent:
+					if isTTY && !askQuiet && len(e.Documents) > 0 {
+						fmt.Fprintf(os.Stderr, "\033[2mFound %d documents\033[0m\n", len(e.Documents))
+					}
+				case models.ReasoningStartEvent:
+					if isTTY && !askQuiet {
+						fmt.Fprintf(os.Stderr, "\033[2mThinking...\033[0m\n")
+					}
+				case models.ToolStartEvent:
+					if isTTY && !askQuiet && e.ToolName != "" {
+						fmt.Fprintf(os.Stderr, "\033[2mUsing %s...\033[0m\n", e.ToolName)
+					}
 				case models.ErrorEvent:
+					ow.Finish()
 					return fmt.Errorf("%s", e.Error)
 				case models.StopEvent:
-					fmt.Println()
+					ow.Finish()
 					return nil
 				}
 			}
 
+			if !askJSON {
+				ow.Finish()
+			}
+
 			if ctx.Err() != nil {
 				if sessionID != "" {
 					client.StopChatSession(context.Background(), sessionID)
 				}
-				if !askJSON {
-					fmt.Println()
-				}
 				return nil
 			}
 
@@ -105,20 +179,56 @@ func newAskCmd() *cobra.Command {
 				return lastErr
 			}
 			if !gotStop {
-				if !askJSON {
-					fmt.Println()
-				}
 				return fmt.Errorf("stream ended unexpectedly")
 			}
-			if !askJSON {
-				fmt.Println()
-			}
 			return nil
 		},
 	}
 
 	cmd.Flags().IntVar(&askAgentID, "agent-id", 0, "Agent ID to use")
 	cmd.Flags().BoolVar(&askJSON, "json", false, "Output raw JSON events")
-	// Suppress cobra's default error/usage on RunE errors
+	cmd.Flags().BoolVarP(&askQuiet, "quiet", "q", false, "Buffer output and print once at end (no streaming)")
+	cmd.Flags().StringVar(&askPrompt, "prompt", "", "Question text (use with piped stdin context)")
+	cmd.Flags().IntVar(&maxOutput, "max-output", defaultMaxOutputBytes,
+		"Max bytes to print before truncating (0 to disable, auto-enabled for non-TTY)")
 	return cmd
 }
+
+// resolveQuestion builds the final question string from args, --prompt, and stdin.
+func resolveQuestion(args []string, prompt string) (string, error) {
+	hasArg := len(args) > 0
+	hasPrompt := prompt != ""
+	hasStdin := !term.IsTerminal(int(os.Stdin.Fd()))
+
+	if hasArg && hasPrompt {
+		return "", exitcodes.New(exitcodes.BadRequest, "specify the question as an argument or --prompt, not both")
+	}
+
+	var stdinContent string
+	if hasStdin {
+		const maxStdinBytes = 10 * 1024 * 1024 // 10MB
+		data, err := io.ReadAll(io.LimitReader(os.Stdin, maxStdinBytes))
+		if err != nil {
+			return "", fmt.Errorf("failed to read stdin: %w", err)
+		}
+		stdinContent = strings.TrimSpace(string(data))
+	}
+
+	switch {
+	case hasArg && stdinContent != "":
+		// arg is the question, stdin is context
+		return args[0] + "\n\n" + stdinContent, nil
+	case hasArg:
+		return args[0], nil
+	case hasPrompt && stdinContent != "":
+		// --prompt is the question, stdin is context
+		return prompt + "\n\n" + stdinContent, nil
+	case hasPrompt:
+		return prompt, nil
+	case stdinContent != "":
+		return stdinContent, nil
+	default:
+		return "", exitcodes.New(exitcodes.BadRequest, "no question provided\n  Usage: onyx-cli ask \"your question\"\n  Or:    echo \"context\" | onyx-cli ask --prompt \"your question\"")
+	}
+}
+

cli/cmd/chat.go

@@ -4,6 +4,7 @@ import (
 	tea "github.com/charmbracelet/bubbletea"
 	"github.com/onyx-dot-app/onyx/cli/internal/config"
 	"github.com/onyx-dot-app/onyx/cli/internal/onboarding"
+	"github.com/onyx-dot-app/onyx/cli/internal/starprompt"
 	"github.com/onyx-dot-app/onyx/cli/internal/tui"
 	"github.com/spf13/cobra"
 )
@@ -12,6 +13,11 @@ func newChatCmd() *cobra.Command {
 	return &cobra.Command{
 		Use:   "chat",
 		Short: "Launch the interactive chat TUI (default)",
+		Long: `Launch the interactive terminal UI for chatting with your Onyx agent.
+This is the default command when no subcommand is specified. On first run,
+an interactive setup wizard will guide you through configuration.`,
+		Example: `  onyx-cli chat
+  onyx-cli`,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			cfg := config.Load()
 
@@ -24,6 +30,8 @@ func newChatCmd() *cobra.Command {
 				cfg = *result
 			}
 
+			starprompt.MaybePrompt()
+
 			m := tui.NewModel(cfg)
 			p := tea.NewProgram(m, tea.WithAltScreen(), tea.WithMouseCellMotion())
 			_, err := p.Run()

cli/cmd/configure.go

@@ -1,19 +1,126 @@
 package cmd
 
 import (
+	"context"
+	"errors"
+	"fmt"
+	"io"
+	"os"
+	"strings"
+	"time"
+
+	"github.com/onyx-dot-app/onyx/cli/internal/api"
 	"github.com/onyx-dot-app/onyx/cli/internal/config"
+	"github.com/onyx-dot-app/onyx/cli/internal/exitcodes"
 	"github.com/onyx-dot-app/onyx/cli/internal/onboarding"
 	"github.com/spf13/cobra"
+	"golang.org/x/term"
 )
 
 func newConfigureCmd() *cobra.Command {
-	return &cobra.Command{
+	var (
+		serverURL   string
+		apiKey      string
+		apiKeyStdin bool
+		dryRun      bool
+	)
+
+	cmd := &cobra.Command{
 		Use:   "configure",
 		Short: "Configure server URL and API key",
+		Long: `Set up the Onyx CLI with your server URL and API key.
+
+When --server-url and --api-key are both provided, the configuration is saved
+non-interactively (useful for scripts and AI agents). Otherwise, an interactive
+setup wizard is launched.
+
+If --api-key is omitted but stdin has piped data, the API key is read from
+stdin automatically. You can also use --api-key-stdin to make this explicit.
+This avoids leaking the key in shell history.
+
+Use --dry-run to test the connection without saving the configuration.`,
+		Example: `  onyx-cli configure
+  onyx-cli configure --server-url https://my-onyx.com --api-key sk-...
+  echo "$ONYX_API_KEY" | onyx-cli configure --server-url https://my-onyx.com
+  echo "$ONYX_API_KEY" | onyx-cli configure --server-url https://my-onyx.com --api-key-stdin
+  onyx-cli configure --server-url https://my-onyx.com --api-key sk-... --dry-run`,
 		RunE: func(cmd *cobra.Command, args []string) error {
+			// Read API key from stdin if piped (implicit) or --api-key-stdin (explicit)
+			if apiKeyStdin && apiKey != "" {
+				return exitcodes.New(exitcodes.BadRequest, "--api-key and --api-key-stdin cannot be used together")
+			}
+			if (apiKey == "" && !term.IsTerminal(int(os.Stdin.Fd()))) || apiKeyStdin {
+				data, err := io.ReadAll(os.Stdin)
+				if err != nil {
+					return fmt.Errorf("failed to read API key from stdin: %w", err)
+				}
+				apiKey = strings.TrimSpace(string(data))
+			}
+
+			if serverURL != "" && apiKey != "" {
+				return configureNonInteractive(serverURL, apiKey, dryRun)
+			}
+
+			if dryRun {
+				return exitcodes.New(exitcodes.BadRequest, "--dry-run requires --server-url and --api-key")
+			}
+
+			if serverURL != "" || apiKey != "" {
+				return exitcodes.New(exitcodes.BadRequest, "both --server-url and --api-key are required for non-interactive setup\n  Run 'onyx-cli configure' without flags for interactive setup")
+			}
+
 			cfg := config.Load()
 			onboarding.Run(&cfg)
 			return nil
 		},
 	}
+
+	cmd.Flags().StringVar(&serverURL, "server-url", "", "Onyx server URL (e.g., https://cloud.onyx.app)")
+	cmd.Flags().StringVar(&apiKey, "api-key", "", "API key for authentication (or pipe via stdin)")
+	cmd.Flags().BoolVar(&apiKeyStdin, "api-key-stdin", false, "Read API key from stdin (explicit; also happens automatically when stdin is piped)")
+	cmd.Flags().BoolVar(&dryRun, "dry-run", false, "Test connection without saving config (requires --server-url and --api-key)")
+
+	return cmd
+}
+
+func configureNonInteractive(serverURL, apiKey string, dryRun bool) error {
+	cfg := config.OnyxCliConfig{
+		ServerURL:      serverURL,
+		APIKey:         apiKey,
+		DefaultAgentID: 0,
+	}
+
+	// Preserve existing default agent ID from disk (not env overrides)
+	if existing := config.LoadFromDisk(); existing.DefaultAgentID != 0 {
+		cfg.DefaultAgentID = existing.DefaultAgentID
+	}
+
+	// Test connection
+	client := api.NewClient(cfg)
+	ctx, cancel := context.WithTimeout(context.Background(), 15*time.Second)
+	defer cancel()
+
+	if err := client.TestConnection(ctx); err != nil {
+		var authErr *api.AuthError
+		if errors.As(err, &authErr) {
+			return exitcodes.Newf(exitcodes.AuthFailure, "authentication failed: %v\n  Check your API key", err)
+		}
+		return exitcodes.Newf(exitcodes.Unreachable, "connection failed: %v\n  Check your server URL", err)
+	}
+
+	if dryRun {
+		fmt.Printf("Server:  %s\n", serverURL)
+		fmt.Println("Status:  connected and authenticated")
+		fmt.Println("Dry run: config was NOT saved")
+		return nil
+	}
+
+	if err := config.Save(cfg); err != nil {
+		return fmt.Errorf("could not save config: %w", err)
+	}
+
+	fmt.Printf("Config:  %s\n", config.ConfigFilePath())
+	fmt.Printf("Server:  %s\n", serverURL)
+	fmt.Println("Status:  connected and authenticated")
+	return nil
 }

cli/cmd/serve.go

@@ -23,6 +23,7 @@ import (
 	"github.com/charmbracelet/wish/ratelimiter"
 	"github.com/onyx-dot-app/onyx/cli/internal/api"
 	"github.com/onyx-dot-app/onyx/cli/internal/config"
+	"github.com/onyx-dot-app/onyx/cli/internal/exitcodes"
 	"github.com/onyx-dot-app/onyx/cli/internal/tui"
 	"github.com/spf13/cobra"
 	"golang.org/x/time/rate"
@@ -295,15 +296,15 @@ provided via the ONYX_API_KEY environment variable to skip the prompt:
 The server URL is taken from the server operator's config. The server
 auto-generates an Ed25519 host key on first run if the key file does not
 already exist. The host key path can also be set via the ONYX_SSH_HOST_KEY
-environment variable (the --host-key flag takes precedence).
-
-Example:
-  onyx-cli serve --port 2222
-  ssh localhost -p 2222`,
+environment variable (the --host-key flag takes precedence).`,
+		Example: `  onyx-cli serve --port 2222
+  ssh localhost -p 2222
+  onyx-cli serve --host 0.0.0.0 --port 2222
+  onyx-cli serve --idle-timeout 30m --max-session-timeout 2h`,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			serverCfg := config.Load()
 			if serverCfg.ServerURL == "" {
-				return fmt.Errorf("server URL is not configured; run 'onyx-cli configure' first")
+				return exitcodes.New(exitcodes.NotConfigured, "server URL is not configured\n  Run: onyx-cli configure")
 			}
 			if !cmd.Flags().Changed("host-key") {
 				if v := os.Getenv(config.EnvSSHHostKey); v != "" {

cli/cmd/validate.go

@@ -2,11 +2,13 @@ package cmd
 
 import (
 	"context"
+	"errors"
 	"fmt"
 	"time"
 
 	"github.com/onyx-dot-app/onyx/cli/internal/api"
 	"github.com/onyx-dot-app/onyx/cli/internal/config"
+	"github.com/onyx-dot-app/onyx/cli/internal/exitcodes"
 	"github.com/onyx-dot-app/onyx/cli/internal/version"
 	log "github.com/sirupsen/logrus"
 	"github.com/spf13/cobra"
@@ -16,17 +18,21 @@ func newValidateConfigCmd() *cobra.Command {
 	return &cobra.Command{
 		Use:   "validate-config",
 		Short: "Validate configuration and test server connection",
+		Long: `Check that the CLI is configured, the server is reachable, and the API key
+is valid. Also reports the server version and warns if it is below the
+minimum required.`,
+		Example: `  onyx-cli validate-config`,
 		RunE: func(cmd *cobra.Command, args []string) error {
 			// Check config file
 			if !config.ConfigExists() {
-				return fmt.Errorf("config file not found at %s\n  Run 'onyx-cli configure' to set up", config.ConfigFilePath())
+				return exitcodes.Newf(exitcodes.NotConfigured, "config file not found at %s\n  Run: onyx-cli configure", config.ConfigFilePath())
 			}
 
 			cfg := config.Load()
 
 			// Check API key
 			if !cfg.IsConfigured() {
-				return fmt.Errorf("API key is missing\n  Run 'onyx-cli configure' to set up")
+				return exitcodes.New(exitcodes.NotConfigured, "API key is missing\n  Run: onyx-cli configure")
 			}
 
 			_, _ = fmt.Fprintf(cmd.OutOrStdout(), "Config:  %s\n", config.ConfigFilePath())
@@ -35,7 +41,11 @@ func newValidateConfigCmd() *cobra.Command {
 			// Test connection
 			client := api.NewClient(cfg)
 			if err := client.TestConnection(cmd.Context()); err != nil {
-				return fmt.Errorf("connection failed: %w", err)
+				var authErr *api.AuthError
+				if errors.As(err, &authErr) {
+					return exitcodes.Newf(exitcodes.AuthFailure, "authentication failed: %v\n  Reconfigure with: onyx-cli configure", err)
+				}
+				return exitcodes.Newf(exitcodes.Unreachable, "connection failed: %v\n  Reconfigure with: onyx-cli configure", err)
 			}
 
 			_, _ = fmt.Fprintln(cmd.OutOrStdout(), "Status:  connected and authenticated")

cli/internal/api/client.go

@@ -149,12 +149,12 @@ func (c *Client) TestConnection(ctx context.Context) error {
 
 	if resp2.StatusCode == 401 || resp2.StatusCode == 403 {
 		if isHTML || strings.Contains(respServer, "awselb") {
-			return fmt.Errorf("HTTP %d from a reverse proxy (not the Onyx backend).\n  Check your deployment's ingress / proxy configuration", resp2.StatusCode)
+			return &AuthError{Message: fmt.Sprintf("HTTP %d from a reverse proxy (not the Onyx backend).\n  Check your deployment's ingress / proxy configuration", resp2.StatusCode)}
 		}
 		if resp2.StatusCode == 401 {
-			return fmt.Errorf("invalid API key or token.\n  %s", body)
+			return &AuthError{Message: fmt.Sprintf("invalid API key or token.\n  %s", body)}
 		}
-		return fmt.Errorf("access denied — check that the API key is valid.\n  %s", body)
+		return &AuthError{Message: fmt.Sprintf("access denied — check that the API key is valid.\n  %s", body)}
 	}
 
 	detail := fmt.Sprintf("HTTP %d", resp2.StatusCode)

cli/internal/api/errors.go

@@ -11,3 +11,12 @@ type OnyxAPIError struct {
 func (e *OnyxAPIError) Error() string {
 	return fmt.Sprintf("HTTP %d: %s", e.StatusCode, e.Detail)
 }
+
+// AuthError is returned when authentication or authorization fails.
+type AuthError struct {
+	Message string
+}
+
+func (e *AuthError) Error() string {
+	return e.Message
+}

cli/internal/config/config.go

@@ -59,8 +59,10 @@ func ConfigExists() bool {
 	return err == nil
 }
 
-// Load reads config from file and applies environment variable overrides.
-func Load() OnyxCliConfig {
+// LoadFromDisk reads config from the file only, without applying environment
+// variable overrides. Use this when you need the persisted config values
+// (e.g., to preserve them during a save operation).
+func LoadFromDisk() OnyxCliConfig {
 	cfg := DefaultConfig()
 
 	data, err := os.ReadFile(ConfigFilePath())
@@ -70,6 +72,13 @@ func Load() OnyxCliConfig {
 		}
 	}
 
+	return cfg
+}
+
+// Load reads config from file and applies environment variable overrides.
+func Load() OnyxCliConfig {
+	cfg := LoadFromDisk()
+
 	// Environment overrides
 	if v := os.Getenv(EnvServerURL); v != "" {
 		cfg.ServerURL = v

cli/internal/exitcodes/codes.go

@@ -0,0 +1,33 @@
+// Package exitcodes defines semantic exit codes for the Onyx CLI.
+package exitcodes
+
+import "fmt"
+
+const (
+	Success       = 0
+	General       = 1
+	BadRequest    = 2 // invalid args / command-line errors (convention)
+	NotConfigured = 3
+	AuthFailure   = 4
+	Unreachable   = 5
+)
+
+// ExitError wraps an error with a specific exit code.
+type ExitError struct {
+	Code int
+	Err  error
+}
+
+func (e *ExitError) Error() string {
+	return e.Err.Error()
+}
+
+// New creates an ExitError with the given code and message.
+func New(code int, msg string) *ExitError {
+	return &ExitError{Code: code, Err: fmt.Errorf("%s", msg)}
+}
+
+// Newf creates an ExitError with a formatted message.
+func Newf(code int, format string, args ...any) *ExitError {
+	return &ExitError{Code: code, Err: fmt.Errorf(format, args...)}
+}

cli/internal/exitcodes/codes_test.go

@@ -0,0 +1,40 @@
+package exitcodes
+
+import (
+	"errors"
+	"fmt"
+	"testing"
+)
+
+func TestExitError_Error(t *testing.T) {
+	e := New(NotConfigured, "not configured")
+	if e.Error() != "not configured" {
+		t.Fatalf("expected 'not configured', got %q", e.Error())
+	}
+	if e.Code != NotConfigured {
+		t.Fatalf("expected code %d, got %d", NotConfigured, e.Code)
+	}
+}
+
+func TestExitError_Newf(t *testing.T) {
+	e := Newf(Unreachable, "cannot reach %s", "server")
+	if e.Error() != "cannot reach server" {
+		t.Fatalf("expected 'cannot reach server', got %q", e.Error())
+	}
+	if e.Code != Unreachable {
+		t.Fatalf("expected code %d, got %d", Unreachable, e.Code)
+	}
+}
+
+func TestExitError_ErrorsAs(t *testing.T) {
+	e := New(BadRequest, "bad input")
+	wrapped := fmt.Errorf("wrapper: %w", e)
+
+	var exitErr *ExitError
+	if !errors.As(wrapped, &exitErr) {
+		t.Fatal("errors.As should find ExitError")
+	}
+	if exitErr.Code != BadRequest {
+		t.Fatalf("expected code %d, got %d", BadRequest, exitErr.Code)
+	}
+}

cli/internal/overflow/writer.go

@@ -0,0 +1,121 @@
+// Package overflow provides a streaming writer that auto-truncates output
+// for non-TTY callers (e.g., AI agents, scripts). Full content is saved to
+// a temp file on disk; only the first N bytes are printed to stdout.
+package overflow
+
+import (
+	"fmt"
+	"os"
+	"strings"
+
+	log "github.com/sirupsen/logrus"
+)
+
+// Writer handles streaming output with optional truncation.
+// When Limit > 0, it streams to a temp file on disk (not memory) and stops
+// writing to stdout after Limit bytes. When Limit == 0, it writes directly
+// to stdout. In Quiet mode, it buffers in memory and prints once at the end.
+type Writer struct {
+	Limit      int
+	Quiet      bool
+	written    int
+	totalBytes int
+	truncated  bool
+	buf        strings.Builder // used only in quiet mode
+	tmpFile    *os.File        // used only in truncation mode (Limit > 0)
+}
+
+// Write sends a chunk of content through the writer.
+func (w *Writer) Write(s string) {
+	w.totalBytes += len(s)
+
+	// Quiet mode: buffer in memory, print nothing
+	if w.Quiet {
+		w.buf.WriteString(s)
+		return
+	}
+
+	if w.Limit <= 0 {
+		fmt.Print(s)
+		return
+	}
+
+	// Truncation mode: stream all content to temp file on disk
+	if w.tmpFile == nil {
+		f, err := os.CreateTemp("", "onyx-ask-*.txt")
+		if err != nil {
+			// Fall back to no-truncation if we can't create the file
+			fmt.Fprintf(os.Stderr, "warning: could not create temp file: %v\n", err)
+			w.Limit = 0
+			fmt.Print(s)
+			return
+		}
+		w.tmpFile = f
+	}
+	if _, err := w.tmpFile.WriteString(s); err != nil {
+		// Disk write failed — abandon truncation, stream directly to stdout
+		fmt.Fprintf(os.Stderr, "warning: temp file write failed: %v\n", err)
+		w.closeTmpFile(true)
+		w.Limit = 0
+		w.truncated = false
+		fmt.Print(s)
+		return
+	}
+
+	if w.truncated {
+		return
+	}
+
+	remaining := w.Limit - w.written
+	if len(s) <= remaining {
+		fmt.Print(s)
+		w.written += len(s)
+	} else {
+		if remaining > 0 {
+			fmt.Print(s[:remaining])
+			w.written += remaining
+		}
+		w.truncated = true
+	}
+}
+
+// Finish flushes remaining output. Call once after all Write calls are done.
+func (w *Writer) Finish() {
+	// Quiet mode: print buffered content at once
+	if w.Quiet {
+		fmt.Println(w.buf.String())
+		return
+	}
+
+	if !w.truncated {
+		w.closeTmpFile(true) // clean up unused temp file
+		fmt.Println()
+		return
+	}
+
+	// Close the temp file so it's readable
+	tmpPath := w.tmpFile.Name()
+	w.closeTmpFile(false) // close but keep the file
+
+	fmt.Printf("\n\n--- response truncated (%d bytes total) ---\n", w.totalBytes)
+	fmt.Printf("Full response: %s\n", tmpPath)
+	fmt.Printf("Explore:\n")
+	fmt.Printf("  cat %s | grep \"<pattern>\"\n", tmpPath)
+	fmt.Printf("  cat %s | tail -50\n", tmpPath)
+}
+
+// closeTmpFile closes and optionally removes the temp file.
+func (w *Writer) closeTmpFile(remove bool) {
+	if w.tmpFile == nil {
+		return
+	}
+	if err := w.tmpFile.Close(); err != nil {
+		log.Debugf("warning: failed to close temp file: %v", err)
+	}
+	if remove {
+		if err := os.Remove(w.tmpFile.Name()); err != nil {
+			log.Debugf("warning: failed to remove temp file: %v", err)
+		}
+	}
+	w.tmpFile = nil
+}

cli/internal/overflow/writer_test.go

@@ -0,0 +1,95 @@
+package overflow
+
+import (
+	"os"
+	"testing"
+)
+
+func TestWriter_NoLimit(t *testing.T) {
+	w := &Writer{Limit: 0}
+	w.Write("hello world")
+	if w.truncated {
+		t.Fatal("should not be truncated with limit 0")
+	}
+	if w.totalBytes != 11 {
+		t.Fatalf("expected 11 total bytes, got %d", w.totalBytes)
+	}
+}
+
+func TestWriter_UnderLimit(t *testing.T) {
+	w := &Writer{Limit: 100}
+	w.Write("hello")
+	w.Write(" world")
+	if w.truncated {
+		t.Fatal("should not be truncated when under limit")
+	}
+	if w.written != 11 {
+		t.Fatalf("expected 11 written bytes, got %d", w.written)
+	}
+}
+
+func TestWriter_OverLimit(t *testing.T) {
+	w := &Writer{Limit: 5}
+	w.Write("hello world") // 11 bytes, limit 5
+	if !w.truncated {
+		t.Fatal("should be truncated")
+	}
+	if w.written != 5 {
+		t.Fatalf("expected 5 written bytes, got %d", w.written)
+	}
+	if w.totalBytes != 11 {
+		t.Fatalf("expected 11 total bytes, got %d", w.totalBytes)
+	}
+	if w.tmpFile == nil {
+		t.Fatal("temp file should have been created")
+	}
+	_ = w.tmpFile.Close()
+	data, _ := os.ReadFile(w.tmpFile.Name())
+	_ = os.Remove(w.tmpFile.Name())
+	if string(data) != "hello world" {
+		t.Fatalf("temp file should contain full content, got %q", string(data))
+	}
+}
+
+func TestWriter_MultipleChunks(t *testing.T) {
+	w := &Writer{Limit: 10}
+	w.Write("hello") // 5 bytes
+	w.Write(" ")     // 6 bytes
+	w.Write("world") // 11 bytes, crosses limit
+	w.Write("!")     // 12 bytes, already truncated
+
+	if !w.truncated {
+		t.Fatal("should be truncated")
+	}
+	if w.written != 10 {
+		t.Fatalf("expected 10 written bytes, got %d", w.written)
+	}
+	if w.totalBytes != 12 {
+		t.Fatalf("expected 12 total bytes, got %d", w.totalBytes)
+	}
+	if w.tmpFile == nil {
+		t.Fatal("temp file should have been created")
+	}
+	_ = w.tmpFile.Close()
+	data, _ := os.ReadFile(w.tmpFile.Name())
+	_ = os.Remove(w.tmpFile.Name())
+	if string(data) != "hello world!" {
+		t.Fatalf("temp file should contain full content, got %q", string(data))
+	}
+}
+
+func TestWriter_QuietMode(t *testing.T) {
+	w := &Writer{Limit: 0, Quiet: true}
+	w.Write("hello")
+	w.Write(" world")
+
+	if w.written != 0 {
+		t.Fatalf("quiet mode should not write to stdout, got %d written", w.written)
+	}
+	if w.totalBytes != 11 {
+		t.Fatalf("expected 11 total bytes, got %d", w.totalBytes)
+	}
+	if w.buf.String() != "hello world" {
+		t.Fatalf("buffer should contain full content, got %q", w.buf.String())
+	}
+}

cli/internal/starprompt/starprompt.go

@@ -0,0 +1,83 @@
+// Package starprompt implements a one-time GitHub star prompt shown before the TUI.
+// Skipped when stdin/stdout is not a TTY, when gh CLI is not installed,
+// or when the user has already been prompted. State is stored in the
+// config directory so it shows at most once per user.
+package starprompt
+
+import (
+	"bufio"
+	"fmt"
+	"os"
+	"os/exec"
+	"path/filepath"
+	"strings"
+	"time"
+
+	"github.com/onyx-dot-app/onyx/cli/internal/config"
+	"golang.org/x/term"
+)
+
+const repo = "onyx-dot-app/onyx"
+
+func statePath() string {
+	return filepath.Join(config.ConfigDir(), ".star-prompted")
+}
+
+func hasBeenPrompted() bool {
+	_, err := os.Stat(statePath())
+	return err == nil
+}
+
+func markPrompted() {
+	_ = os.MkdirAll(config.ConfigDir(), 0o755)
+	f, err := os.Create(statePath())
+	if err == nil {
+		_ = f.Close()
+	}
+}
+
+func isGHInstalled() bool {
+	_, err := exec.LookPath("gh")
+	return err == nil
+}
+
+// MaybePrompt shows a one-time star prompt if conditions are met.
+// It is safe to call unconditionally — it no-ops when not appropriate.
+func MaybePrompt() {
+	if !term.IsTerminal(int(os.Stdin.Fd())) || !term.IsTerminal(int(os.Stdout.Fd())) {
+		return
+	}
+	if hasBeenPrompted() {
+		return
+	}
+	if !isGHInstalled() {
+		return
+	}
+
+	// Mark before asking so Ctrl+C won't cause a re-prompt.
+	markPrompted()
+
+	fmt.Print("Enjoying Onyx? Star the repo on GitHub? [Y/n] ")
+	reader := bufio.NewReader(os.Stdin)
+	answer, _ := reader.ReadString('\n')
+	answer = strings.TrimSpace(strings.ToLower(answer))
+
+	if answer == "n" || answer == "no" {
+		return
+	}
+
+	cmd := exec.Command("gh", "api", "-X", "PUT", "/user/starred/"+repo)
+	cmd.Env = append(os.Environ(), "GH_PAGER=")
+	if devnull, err := os.Open(os.DevNull); err == nil {
+		defer func() { _ = devnull.Close() }()
+		cmd.Stdin = devnull
+		cmd.Stdout = devnull
+		cmd.Stderr = devnull
+	}
+	if err := cmd.Run(); err != nil {
+		fmt.Println("Star us at: https://github.com/" + repo)
+	} else {
+		fmt.Println("Thanks for the star!")
+		time.Sleep(500 * time.Millisecond)
+	}
+}

cli/main.go

@@ -1,10 +1,12 @@
 package main
 
 import (
+	"errors"
 	"fmt"
 	"os"
 
 	"github.com/onyx-dot-app/onyx/cli/cmd"
+	"github.com/onyx-dot-app/onyx/cli/internal/exitcodes"
 )
 
 var (
@@ -18,6 +20,10 @@ func main() {
 
 	if err := cmd.Execute(); err != nil {
 		fmt.Fprintf(os.Stderr, "Error: %v\n", err)
+		var exitErr *exitcodes.ExitError
+		if errors.As(err, &exitErr) {
+			os.Exit(exitErr.Code)
+		}
 		os.Exit(1)
 	}
 }

deployment/docker_compose/install.sh

@@ -1302,4 +1302,18 @@ echo ""
 print_info "Refer to the README in the ${INSTALL_ROOT} directory for more information."
 echo ""
 print_info "For help or issues, contact: founders@onyx.app"
-echo ""
+echo ""
+
+# --- GitHub star prompt (inspired by oh-my-codex) ---
+# Only prompt in interactive mode and only if gh CLI is available.
+# Uses the GitHub API directly (PUT /user/starred) like oh-my-codex.
+if is_interactive && command -v gh &>/dev/null; then
+    prompt_yn_or_default "Enjoying Onyx? Star the repo on GitHub? [Y/n] " "Y"
+    if [[ ! "$REPLY" =~ ^[Nn] ]]; then
+        if GH_PAGER= gh api -X PUT /user/starred/onyx-dot-app/onyx < /dev/null >/dev/null 2>&1; then
+            print_success "Thanks for the star!"
+        else
+            print_info "Star us at: https://github.com/onyx-dot-app/onyx"
+        fi
+    fi
+fi

web/AGENTS.md

@@ -193,9 +193,9 @@ hover, active, and disabled states.
 
 ### Disabled (`core/disabled/`)
 
-Propagates disabled state via React context. `Interactive.Stateless` and `Interactive.Stateful`
-consume this automatically, so wrapping a subtree in `<Disabled disabled={true}>` disables all
-interactive descendants.
+A pure CSS wrapper that applies disabled visuals (`opacity-50`, `cursor-not-allowed`,
+`pointer-events: none`) to a single child element via Radix `Slot`. Has no React context —
+Interactive primitives and buttons manage their own disabled state via a `disabled` prop.
 
 ### Hoverable (`core/animations/`)
 

web/lib/opal/src/components/buttons/button/components.tsx

@@ -1,9 +1,5 @@
 import "@opal/components/tooltip.css";
-import {
-  Disabled,
-  Interactive,
-  type InteractiveStatelessProps,
-} from "@opal/core";
+import { Interactive, type InteractiveStatelessProps } from "@opal/core";
 import type {
   ContainerSizeVariants,
   ExtremaSizeVariants,
@@ -49,7 +45,7 @@ type ButtonProps = InteractiveStatelessProps &
     /** Which side the tooltip appears on. */
     tooltipSide?: TooltipSide;
 
-    /** Wraps the button in a Disabled context. `false` overrides parent contexts. */
+    /** Applies disabled styling and suppresses clicks. */
     disabled?: boolean;
   };
 
@@ -94,7 +90,11 @@ function Button({
   ) : null;
 
   const button = (
-    <Interactive.Stateless type={type} {...interactiveProps}>
+    <Interactive.Stateless
+      type={type}
+      disabled={disabled}
+      {...interactiveProps}
+    >
       <Interactive.Container
         type={type}
         border={interactiveProps.prominence === "secondary"}
@@ -118,28 +118,24 @@ function Button({
     </Interactive.Stateless>
   );
 
-  const result = tooltip ? (
-    <TooltipPrimitive.Root>
-      <TooltipPrimitive.Trigger asChild>{button}</TooltipPrimitive.Trigger>
-      <TooltipPrimitive.Portal>
-        <TooltipPrimitive.Content
-          className="opal-tooltip"
-          side={tooltipSide}
-          sideOffset={4}
-        >
-          {tooltip}
-        </TooltipPrimitive.Content>
-      </TooltipPrimitive.Portal>
-    </TooltipPrimitive.Root>
-  ) : (
-    button
-  );
-
-  if (disabled != null) {
-    return <Disabled disabled={disabled}>{result}</Disabled>;
+  if (tooltip) {
+    return (
+      <TooltipPrimitive.Root>
+        <TooltipPrimitive.Trigger asChild>{button}</TooltipPrimitive.Trigger>
+        <TooltipPrimitive.Portal>
+          <TooltipPrimitive.Content
+            className="opal-tooltip"
+            side={tooltipSide}
+            sideOffset={4}
+          >
+            {tooltip}
+          </TooltipPrimitive.Content>
+        </TooltipPrimitive.Portal>
+      </TooltipPrimitive.Root>
+    );
   }
 
-  return result;
+  return button;
 }
 
 export { Button, type ButtonProps };

web/lib/opal/src/components/buttons/open-button/components.tsx

@@ -1,6 +1,5 @@
 import {
   Interactive,
-  useDisabled,
   type InteractiveStatefulProps,
   type InteractiveStatefulInteraction,
 } from "@opal/core";
@@ -74,6 +73,9 @@ type OpenButtonProps = Omit<InteractiveStatefulProps, "variant"> & {
 
     /** Override the default rounding derived from `size`. */
     roundingVariant?: InteractiveContainerRoundingVariant;
+
+    /** Applies disabled styling and suppresses clicks. */
+    disabled?: boolean;
   };
 
 // ---------------------------------------------------------------------------
@@ -92,10 +94,9 @@ function OpenButton({
   roundingVariant: roundingVariantOverride,
   interaction,
   variant = "select-heavy",
+  disabled,
   ...statefulProps
 }: OpenButtonProps) {
-  const { isDisabled } = useDisabled();
-
   // Derive open state: explicit prop → Radix data-state (injected via Slot chain)
   const dataState = (statefulProps as Record<string, unknown>)["data-state"] as
     | string
@@ -119,6 +120,7 @@ function OpenButton({
     <Interactive.Stateful
       variant={variant}
       interaction={resolvedInteraction}
+      disabled={disabled}
       {...statefulProps}
     >
       <Interactive.Container
@@ -168,7 +170,7 @@ function OpenButton({
   );
 
   const resolvedTooltip =
-    tooltip ?? (foldable && isDisabled && children ? children : undefined);
+    tooltip ?? (foldable && disabled && children ? children : undefined);
 
   if (!resolvedTooltip) return button;
 

web/lib/opal/src/components/buttons/select-button/components.tsx

@@ -1,11 +1,7 @@
 "use client";
 
 import "@opal/components/buttons/select-button/styles.css";
-import {
-  Interactive,
-  useDisabled,
-  type InteractiveStatefulProps,
-} from "@opal/core";
+import { Interactive, type InteractiveStatefulProps } from "@opal/core";
 import type {
   ContainerSizeVariants,
   ExtremaSizeVariants,
@@ -64,6 +60,9 @@ type SelectButtonProps = InteractiveStatefulProps &
 
     /** Which side the tooltip appears on. */
     tooltipSide?: TooltipSide;
+
+    /** Applies disabled styling and suppresses clicks. */
+    disabled?: boolean;
   };
 
 // ---------------------------------------------------------------------------
@@ -80,9 +79,9 @@ function SelectButton({
   width,
   tooltip,
   tooltipSide = "top",
+  disabled,
   ...statefulProps
 }: SelectButtonProps) {
-  const { isDisabled } = useDisabled();
   const isLarge = size === "lg";
 
   const labelEl = children ? (
@@ -96,7 +95,7 @@ function SelectButton({
   ) : null;
 
   const button = (
-    <Interactive.Stateful {...statefulProps}>
+    <Interactive.Stateful disabled={disabled} {...statefulProps}>
       <Interactive.Container
         type={type}
         heightVariant={size}
@@ -128,7 +127,7 @@ function SelectButton({
   );
 
   const resolvedTooltip =
-    tooltip ?? (foldable && isDisabled && children ? children : undefined);
+    tooltip ?? (foldable && disabled && children ? children : undefined);
 
   if (!resolvedTooltip) return button;
 

web/lib/opal/src/components/buttons/sidebar-tab/README.md

@@ -0,0 +1,64 @@
+# SidebarTab
+
+**Import:** `import { SidebarTab, type SidebarTabProps } from "@opal/components";`
+
+A sidebar navigation tab built on `Interactive.Stateful` > `Interactive.Container`. Designed for admin and app sidebars.
+
+## Architecture
+
+```
+div.relative
+  └─ Interactive.Stateful        <- variant (sidebar-heavy | sidebar-light), state, disabled
+       └─ Interactive.Container  <- rounding, height, width
+            ├─ Link?             (absolute overlay for client-side navigation)
+            ├─ rightChildren?    (absolute, above Link for inline actions)
+            └─ ContentAction     (icon + title + truncation spacer)
+```
+
+- **`sidebar-heavy`** (default) — muted when unselected (text-03/text-02), bold when selected (text-04/text-03)
+- **`sidebar-light`** — uniformly muted across all states (text-02/text-02)
+- **Disabled** — both variants use text-02 foreground, transparent background, no hover/active states
+- **Navigation** uses an absolutely positioned `<Link>` overlay rather than `href` on the Interactive element, so `rightChildren` can sit above it with `pointer-events-auto`.
+
+## Props
+
+| Prop | Type | Default | Description |
+|------|------|---------|-------------|
+| `variant` | `"sidebar-heavy" \| "sidebar-light"` | `"sidebar-heavy"` | Sidebar color variant |
+| `selected` | `boolean` | `false` | Active/selected state |
+| `icon` | `IconFunctionComponent` | — | Left icon |
+| `children` | `ReactNode` | — | Label text or custom content |
+| `disabled` | `boolean` | `false` | Disables the tab |
+| `folded` | `boolean` | `false` | Collapses label, shows tooltip on hover |
+| `nested` | `boolean` | `false` | Renders spacer instead of icon for indented items |
+| `href` | `string` | — | Client-side navigation URL |
+| `onClick` | `MouseEventHandler` | — | Click handler |
+| `type` | `ButtonType` | — | HTML button type |
+| `rightChildren` | `ReactNode` | — | Actions rendered on the right side |
+
+## Usage
+
+```tsx
+import { SidebarTab } from "@opal/components";
+import { SvgSettings, SvgLock } from "@opal/icons";
+
+// Active tab
+<SidebarTab icon={SvgSettings} href="/admin/settings" selected>
+  Settings
+</SidebarTab>
+
+// Muted variant
+<SidebarTab icon={SvgSettings} variant="sidebar-light">
+  Exit Admin Panel
+</SidebarTab>
+
+// Disabled enterprise-only tab
+<SidebarTab icon={SvgLock} disabled>
+  Groups
+</SidebarTab>
+
+// Folded sidebar (icon only, tooltip on hover)
+<SidebarTab icon={SvgSettings} href="/admin/settings" folded>
+  Settings
+</SidebarTab>
+```

web/lib/opal/src/components/buttons/sidebar-tab/SidebarTab.stories.tsx

@@ -0,0 +1,94 @@
+import type { Meta, StoryObj } from "@storybook/react";
+import { SidebarTab } from "@opal/components/buttons/sidebar-tab/components";
+import {
+  SvgSettings,
+  SvgUsers,
+  SvgLock,
+  SvgArrowUpCircle,
+  SvgTrash,
+} from "@opal/icons";
+import { Button } from "@opal/components";
+import * as TooltipPrimitive from "@radix-ui/react-tooltip";
+
+const meta: Meta<typeof SidebarTab> = {
+  title: "opal/components/SidebarTab",
+  component: SidebarTab,
+  tags: ["autodocs"],
+  decorators: [
+    (Story) => (
+      <TooltipPrimitive.Provider>
+        <div style={{ width: 260, background: "var(--background-neutral-01)" }}>
+          <Story />
+        </div>
+      </TooltipPrimitive.Provider>
+    ),
+  ],
+};
+
+export default meta;
+type Story = StoryObj<typeof SidebarTab>;
+
+export const Default: Story = {
+  args: {
+    icon: SvgSettings,
+    children: "Settings",
+  },
+};
+
+export const Selected: Story = {
+  args: {
+    icon: SvgSettings,
+    children: "Settings",
+    selected: true,
+  },
+};
+
+export const Light: Story = {
+  args: {
+    icon: SvgSettings,
+    children: "Settings",
+    variant: "sidebar-light",
+  },
+};
+
+export const Disabled: Story = {
+  args: {
+    icon: SvgLock,
+    children: "Enterprise Only",
+    disabled: true,
+  },
+};
+
+export const WithRightChildren: Story = {
+  args: {
+    icon: SvgUsers,
+    children: "Users",
+    rightChildren: (
+      <Button
+        icon={SvgTrash}
+        size="xs"
+        prominence="tertiary"
+        variant="danger"
+      />
+    ),
+  },
+};
+
+export const SidebarExample: Story = {
+  render: () => (
+    <div className="flex flex-col">
+      <SidebarTab icon={SvgSettings} selected>
+        LLM Models
+      </SidebarTab>
+      <SidebarTab icon={SvgSettings}>Web Search</SidebarTab>
+      <SidebarTab icon={SvgUsers}>Users</SidebarTab>
+      <SidebarTab icon={SvgLock} disabled>
+        Groups
+      </SidebarTab>
+      <SidebarTab icon={SvgLock} disabled>
+        SCIM
+      </SidebarTab>
+      <SidebarTab icon={SvgArrowUpCircle}>Upgrade Plan</SidebarTab>
+    </div>
+  ),
+};

web/lib/opal/src/components/buttons/sidebar-tab/components.tsx

@@ -3,32 +3,66 @@
 import React from "react";
 import type { ButtonType, IconFunctionComponent } from "@opal/types";
 import type { Route } from "next";
-import { Interactive } from "@opal/core";
+import { Interactive, type InteractiveStatefulVariant } from "@opal/core";
 import { ContentAction } from "@opal/layouts";
+import { Text } from "@opal/components";
 import Link from "next/link";
-import SimpleTooltip from "@/refresh-components/SimpleTooltip";
+import * as TooltipPrimitive from "@radix-ui/react-tooltip";
+import "@opal/components/tooltip.css";
 
-export interface SidebarTabProps {
-  // Button states:
+// ---------------------------------------------------------------------------
+// Types
+// ---------------------------------------------------------------------------
+
+interface SidebarTabProps {
+  /** Collapses the label, showing only the icon. */
   folded?: boolean;
+
+  /** Marks this tab as the currently active/selected item. */
   selected?: boolean;
-  lowlight?: boolean;
+
+  /**
+   * Sidebar color variant.
+   * @default "sidebar-heavy"
+   */
+  variant?: Extract<
+    InteractiveStatefulVariant,
+    "sidebar-light" | "sidebar-heavy"
+  >;
+
+  /** Renders an empty spacer in place of the icon for nested items. */
   nested?: boolean;
 
-  // Button properties:
+  /** Disables the tab — applies muted colors and suppresses clicks. */
+  disabled?: boolean;
+
   onClick?: React.MouseEventHandler<HTMLElement>;
   href?: string;
   type?: ButtonType;
   icon?: IconFunctionComponent;
   children?: React.ReactNode;
+
+  /** Content rendered on the right side (e.g. action buttons). */
   rightChildren?: React.ReactNode;
 }
 
-export default function SidebarTab({
+// ---------------------------------------------------------------------------
+// SidebarTab
+// ---------------------------------------------------------------------------
+
+/**
+ * Sidebar navigation tab built on `Interactive.Stateful` > `Interactive.Container`.
+ *
+ * Uses `sidebar-heavy` (default) or `sidebar-light` (via `variant`) variants
+ * for color styling. Supports an overlay `Link` for client-side navigation,
+ * `rightChildren` for inline actions, and folded mode with an auto-tooltip.
+ */
+function SidebarTab({
   folded,
   selected,
-  lowlight,
+  variant = "sidebar-heavy",
   nested,
+  disabled,
 
   onClick,
   href,
@@ -45,11 +79,8 @@ export default function SidebarTab({
         )) as IconFunctionComponent)
       : null);
 
-  // NOTE (@raunakab)
-  //
-  // The `rightChildren` node NEEDS to be absolutely positioned since it needs to live on top of the absolutely positioned `Link`.
-  // However, having the `rightChildren` be absolutely positioned means that it cannot appropriately truncate the title.
-  // Therefore, we add a dummy node solely for the truncation effects that we obtain.
+  // The `rightChildren` node is absolutely positioned to sit on top of the
+  // overlay Link. A zero-width spacer reserves truncation space for the title.
   const truncationSpacer = rightChildren && (
     <div className="w-0 group-hover/SidebarTab:w-6" />
   );
@@ -57,8 +88,9 @@ export default function SidebarTab({
   const content = (
     <div className="relative">
       <Interactive.Stateful
-        variant={lowlight ? "sidebar-light" : "sidebar-heavy"}
+        variant={variant}
         state={selected ? "selected" : "empty"}
+        disabled={disabled}
         onClick={onClick}
         type="button"
         group="group/SidebarTab"
@@ -69,7 +101,7 @@ export default function SidebarTab({
           widthVariant="full"
           type={type}
         >
-          {href && (
+          {href && !disabled && (
             <Link
               href={href as Route}
               scroll={false}
@@ -102,12 +134,7 @@ export default function SidebarTab({
                 </div>
               )}
               {children}
-              {
-                // NOTE (@raunakab)
-                //
-                // Adding the `truncationSpacer` here for the same reason as above.
-                truncationSpacer
-              }
+              {truncationSpacer}
             </div>
           )}
         </Interactive.Container>
@@ -116,7 +143,23 @@ export default function SidebarTab({
   );
 
   if (typeof children !== "string") return content;
-  if (folded)
-    return <SimpleTooltip tooltip={children}>{content}</SimpleTooltip>;
+  if (folded) {
+    return (
+      <TooltipPrimitive.Root>
+        <TooltipPrimitive.Trigger asChild>{content}</TooltipPrimitive.Trigger>
+        <TooltipPrimitive.Portal>
+          <TooltipPrimitive.Content
+            className="opal-tooltip"
+            side="right"
+            sideOffset={4}
+          >
+            <Text>{children}</Text>
+          </TooltipPrimitive.Content>
+        </TooltipPrimitive.Portal>
+      </TooltipPrimitive.Root>
+    );
+  }
   return content;
 }
+
+export { SidebarTab, type SidebarTabProps };

web/lib/opal/src/components/index.ts

@@ -33,6 +33,12 @@ export {
   type LineItemButtonProps,
 } from "@opal/components/buttons/line-item-button/components";
 
+/* SidebarTab */
+export {
+  SidebarTab,
+  type SidebarTabProps,
+} from "@opal/components/buttons/sidebar-tab/components";
+
 /* Text */
 export {
   Text,

web/lib/opal/src/components/table/components.tsx

@@ -586,7 +586,10 @@ export function Table<TData>(props: DataTableProps<TData>) {
 
                       // Data / Display cell
                       return (
-                        <TableCell key={cell.id}>
+                        <TableCell
+                          key={cell.id}
+                          data-column-id={cell.column.id}
+                        >
                           {flexRender(
                             cell.column.columnDef.cell,
                             cell.getContext()

web/lib/opal/src/core/disabled/components.tsx

@@ -1,33 +1,7 @@
-"use client";
-
 import "@opal/core/disabled/styles.css";
-import React, { createContext, useContext } from "react";
+import React from "react";
 import { Slot } from "@radix-ui/react-slot";
 
-// ---------------------------------------------------------------------------
-// Context
-// ---------------------------------------------------------------------------
-
-interface DisabledContextValue {
-  isDisabled: boolean;
-  allowClick: boolean;
-}
-
-const DisabledContext = createContext<DisabledContextValue>({
-  isDisabled: false,
-  allowClick: false,
-});
-
-/**
- * Returns the current disabled state from the nearest `<Disabled>` ancestor.
- *
- * Used internally by `Interactive.Stateless` and `Interactive.Stateful` to
- * derive `data-disabled` and `aria-disabled` attributes automatically.
- */
-function useDisabled(): DisabledContextValue {
-  return useContext(DisabledContext);
-}
-
 // ---------------------------------------------------------------------------
 // Types
 // ---------------------------------------------------------------------------
@@ -56,8 +30,8 @@ interface DisabledProps extends React.HTMLAttributes<HTMLElement> {
 // ---------------------------------------------------------------------------
 
 /**
- * Wrapper component that propagates disabled state via context and applies
- * baseline disabled CSS (opacity, cursor, pointer-events) to its child.
+ * Wrapper component that applies baseline disabled CSS (opacity, cursor,
+ * pointer-events) to its child element.
  *
  * Uses Radix `Slot` — merges props onto the single child element without
  * adding any DOM node. Works correctly inside Radix `asChild` chains.
@@ -65,7 +39,7 @@ interface DisabledProps extends React.HTMLAttributes<HTMLElement> {
  * @example
  * ```tsx
  * <Disabled disabled={!canSubmit}>
- *   <Button onClick={handleSubmit}>Save</Button>
+ *   <div>...</div>
  * </Disabled>
  * ```
  */
@@ -77,20 +51,16 @@ function Disabled({
   ...rest
 }: DisabledProps) {
   return (
-    <DisabledContext.Provider
-      value={{ isDisabled: !!disabled, allowClick: !!allowClick }}
+    <Slot
+      ref={ref}
+      {...rest}
+      aria-disabled={disabled || undefined}
+      data-opal-disabled={disabled || undefined}
+      data-allow-click={disabled && allowClick ? "" : undefined}
     >
-      <Slot
-        ref={ref}
-        {...rest}
-        aria-disabled={disabled || undefined}
-        data-opal-disabled={disabled || undefined}
-        data-allow-click={disabled && allowClick ? "" : undefined}
-      >
-        {children}
-      </Slot>
-    </DisabledContext.Provider>
+      {children}
+    </Slot>
   );
 }
 
-export { Disabled, useDisabled, type DisabledProps, type DisabledContextValue };
+export { Disabled, type DisabledProps };

web/lib/opal/src/core/index.ts

@@ -1,10 +1,5 @@
 /* Disabled */
-export {
-  Disabled,
-  useDisabled,
-  type DisabledProps,
-  type DisabledContextValue,
-} from "@opal/core/disabled/components";
+export { Disabled, type DisabledProps } from "@opal/core/disabled/components";
 
 /* Animations (formerly Hoverable) */
 export {

web/lib/opal/src/core/interactive/container/components.tsx

@@ -10,7 +10,6 @@ import {
   widthVariants,
   type ExtremaSizeVariants,
 } from "@opal/shared";
-import { useDisabled } from "@opal/core/disabled/components";
 
 // ---------------------------------------------------------------------------
 // Types
@@ -102,7 +101,6 @@ function InteractiveContainer({
   widthVariant = "fit",
   ...props
 }: InteractiveContainerProps) {
-  const { allowClick } = useDisabled();
   const {
     className: slotClassName,
     style: slotStyle,
@@ -148,8 +146,7 @@ function InteractiveContainer({
   if (type) {
     const ariaDisabled = (rest as Record<string, unknown>)["aria-disabled"];
     const nativeDisabled =
-      (type === "submit" || !allowClick) &&
-      (ariaDisabled === true || ariaDisabled === "true" || undefined);
+      ariaDisabled === true || ariaDisabled === "true" || undefined;
     return (
       <button
         ref={ref as React.Ref<HTMLButtonElement>}

web/lib/opal/src/core/interactive/simple/components.tsx

@@ -1,7 +1,6 @@
 import React from "react";
 import { Slot } from "@radix-ui/react-slot";
 import { cn } from "@opal/utils";
-import { useDisabled } from "@opal/core/disabled/components";
 import { guardPortalClick } from "@opal/core/interactive/utils";
 
 // ---------------------------------------------------------------------------
@@ -29,6 +28,11 @@ interface InteractiveSimpleProps
    * Link target (e.g. `"_blank"`). Only used when `href` is provided.
    */
   target?: string;
+
+  /**
+   * Applies disabled cursor and suppresses clicks.
+   */
+  disabled?: boolean;
 }
 
 // ---------------------------------------------------------------------------
@@ -38,8 +42,8 @@ interface InteractiveSimpleProps
 /**
  * Minimal interactive surface primitive.
  *
- * Provides cursor styling, click handling, disabled integration, and
- * optional link/group support — but **no color or background styling**.
+ * Provides cursor styling, click handling, and optional link/group
+ * support — but **no color or background styling**.
  *
  * Use this for elements that need interactivity (click, cursor, disabled)
  * without participating in the Interactive color system.
@@ -59,9 +63,10 @@ function InteractiveSimple({
   group,
   href,
   target,
+  disabled,
   ...props
 }: InteractiveSimpleProps) {
-  const { isDisabled, allowClick } = useDisabled();
+  const isDisabled = !!disabled;
 
   const classes = cn(
     "cursor-pointer select-none",
@@ -88,7 +93,7 @@ function InteractiveSimple({
       {...linkAttrs}
       {...slotProps}
       onClick={
-        isDisabled && !allowClick
+        isDisabled
           ? href
             ? (e: React.MouseEvent) => e.preventDefault()
             : undefined

web/lib/opal/src/core/interactive/stateful/components.tsx

@@ -3,7 +3,6 @@ import "@opal/core/interactive/stateful/styles.css";
 import React from "react";
 import { Slot } from "@radix-ui/react-slot";
 import { cn } from "@opal/utils";
-import { useDisabled } from "@opal/core/disabled/components";
 import { guardPortalClick } from "@opal/core/interactive/utils";
 import type { ButtonType, WithoutStyles } from "@opal/types";
 
@@ -87,6 +86,11 @@ interface InteractiveStatefulProps
    * Link target (e.g. `"_blank"`). Only used when `href` is provided.
    */
   target?: string;
+
+  /**
+   * Applies variant-specific disabled colors and suppresses clicks.
+   */
+  disabled?: boolean;
 }
 
 // ---------------------------------------------------------------------------
@@ -100,8 +104,7 @@ interface InteractiveStatefulProps
  * (empty/filled/selected). Applies variant/state color styling via CSS
  * data-attributes and merges onto a single child element via Radix `Slot`.
  *
- * Disabled state is consumed from the nearest `<Disabled>` ancestor via
- * context — there is no `disabled` prop on this component.
+ * Disabled state is controlled via the `disabled` prop.
  */
 function InteractiveStateful({
   ref,
@@ -112,9 +115,10 @@ function InteractiveStateful({
   type,
   href,
   target,
+  disabled,
   ...props
 }: InteractiveStatefulProps) {
-  const { isDisabled, allowClick } = useDisabled();
+  const isDisabled = !!disabled;
 
   // onClick/href are always passed directly — Stateful is the outermost Slot,
   // so Radix Slot-injected handlers don't bypass this guard.
@@ -150,7 +154,7 @@ function InteractiveStateful({
       {...linkAttrs}
       {...slotProps}
       onClick={
-        isDisabled && !allowClick
+        isDisabled
           ? href
             ? (e: React.MouseEvent) => e.preventDefault()
             : undefined

web/lib/opal/src/core/interactive/stateful/styles.css

@@ -550,6 +550,14 @@
   ) {
   @apply bg-background-tint-03;
 }
+/* ---------------------------------------------------------------------------
+   Sidebar-Heavy — Disabled (all states)
+   --------------------------------------------------------------------------- */
+.interactive[data-interactive-variant="sidebar-heavy"][data-disabled] {
+  @apply bg-transparent opacity-50;
+  --interactive-foreground: var(--text-03);
+  --interactive-foreground-icon: var(--text-03);
+}
 
 /* ===========================================================================
    Sidebar-Light
@@ -607,3 +615,11 @@
   ) {
   @apply bg-background-tint-03;
 }
+/* ---------------------------------------------------------------------------
+   Sidebar-Light — Disabled (all states)
+   --------------------------------------------------------------------------- */
+.interactive[data-interactive-variant="sidebar-light"][data-disabled] {
+  @apply bg-transparent opacity-50;
+  --interactive-foreground: var(--text-03);
+  --interactive-foreground-icon: var(--text-03);
+}

web/lib/opal/src/core/interactive/stateless/components.tsx

@@ -3,7 +3,6 @@ import "@opal/core/interactive/stateless/styles.css";
 import React from "react";
 import { Slot } from "@radix-ui/react-slot";
 import { cn } from "@opal/utils";
-import { useDisabled } from "@opal/core/disabled/components";
 import { guardPortalClick } from "@opal/core/interactive/utils";
 import type { ButtonType, WithoutStyles } from "@opal/types";
 
@@ -70,6 +69,11 @@ interface InteractiveStatelessProps
    * Link target (e.g. `"_blank"`). Only used when `href` is provided.
    */
   target?: string;
+
+  /**
+   * Applies variant-specific disabled colors and suppresses clicks.
+   */
+  disabled?: boolean;
 }
 
 // ---------------------------------------------------------------------------
@@ -84,8 +88,7 @@ interface InteractiveStatelessProps
  * color styling via CSS data-attributes and merges onto a single child
  * element via Radix `Slot`.
  *
- * Disabled state is consumed from the nearest `<Disabled>` ancestor via
- * context — there is no `disabled` prop on this component.
+ * Disabled state is controlled via the `disabled` prop.
  */
 function InteractiveStateless({
   ref,
@@ -96,9 +99,10 @@ function InteractiveStateless({
   type,
   href,
   target,
+  disabled,
   ...props
 }: InteractiveStatelessProps) {
-  const { isDisabled, allowClick } = useDisabled();
+  const isDisabled = !!disabled;
 
   // onClick/href are always passed directly — Stateless is the outermost Slot,
   // so Radix Slot-injected handlers don't bypass this guard.
@@ -134,7 +138,7 @@ function InteractiveStateless({
       {...linkAttrs}
       {...slotProps}
       onClick={
-        isDisabled && !allowClick
+        isDisabled
           ? href
             ? (e: React.MouseEvent) => e.preventDefault()
             : undefined

web/src/app/admin/billing/BillingDetailsView.tsx

@@ -8,7 +8,6 @@ import * as InputLayouts from "@/layouts/input-layouts";
 import Card from "@/refresh-components/cards/Card";
 import Button from "@/refresh-components/buttons/Button";
 import { Button as OpalButton } from "@opal/components";
-import { Disabled } from "@opal/core";
 import Text from "@/refresh-components/texts/Text";
 import Message from "@/refresh-components/messages/Message";
 import InfoBlock from "@/refresh-components/messages/InfoBlock";
@@ -246,15 +245,14 @@ function SubscriptionCard({
               to make changes.
             </Text>
           ) : disabled ? (
-            <Disabled disabled={isReconnecting}>
-              <OpalButton
-                prominence="secondary"
-                onClick={handleReconnect}
-                rightIcon={SvgArrowRight}
-              >
-                {isReconnecting ? "Connecting..." : "Connect to Stripe"}
-              </OpalButton>
-            </Disabled>
+            <OpalButton
+              disabled={isReconnecting}
+              prominence="secondary"
+              onClick={handleReconnect}
+              rightIcon={SvgArrowRight}
+            >
+              {isReconnecting ? "Connecting..." : "Connect to Stripe"}
+            </OpalButton>
           ) : (
             <OpalButton onClick={handleManagePlan} rightIcon={SvgExternalLink}>
               Manage Plan
@@ -377,11 +375,13 @@ function SeatsCard({
             sizePreset="main-content"
             variant="section"
           />
-          <Disabled disabled={isSubmitting}>
-            <OpalButton prominence="secondary" onClick={handleCancel}>
-              Cancel
-            </OpalButton>
-          </Disabled>
+          <OpalButton
+            disabled={isSubmitting}
+            prominence="secondary"
+            onClick={handleCancel}
+          >
+            Cancel
+          </OpalButton>
         </Section>
 
         <div className="billing-content-area">
@@ -463,15 +463,14 @@ function SeatsCard({
               No changes to your billing.
             </Text>
           )}
-          <Disabled
+          <OpalButton
             disabled={
               isSubmitting || newSeatCount === totalSeats || isBelowMinimum
             }
+            onClick={handleConfirm}
           >
-            <OpalButton onClick={handleConfirm}>
-              {isSubmitting ? "Saving..." : "Confirm Change"}
-            </OpalButton>
-          </Disabled>
+            {isSubmitting ? "Saving..." : "Confirm Change"}
+          </OpalButton>
         </Section>
       </Card>
     );
@@ -509,15 +508,14 @@ function SeatsCard({
             View Users
           </OpalButton>
           {!hideUpdateSeats && (
-            <Disabled disabled={isLoadingUsers || disabled || !billing}>
-              <OpalButton
-                prominence="secondary"
-                onClick={handleStartEdit}
-                icon={SvgPlus}
-              >
-                Update Seats
-              </OpalButton>
-            </Disabled>
+            <OpalButton
+              disabled={isLoadingUsers || disabled || !billing}
+              prominence="secondary"
+              onClick={handleStartEdit}
+              icon={SvgPlus}
+            >
+              Update Seats
+            </OpalButton>
           )}
         </Section>
       </Section>

web/src/app/admin/billing/CheckoutView.tsx

@@ -4,7 +4,6 @@ import { useState, useMemo, useEffect } from "react";
 import { Section } from "@/layouts/general-layouts";
 import * as InputLayouts from "@/layouts/input-layouts";
 import { Button } from "@opal/components";
-import { Disabled } from "@opal/core";
 import Text from "@/refresh-components/texts/Text";
 import Card from "@/refresh-components/cards/Card";
 import Separator from "@/refresh-components/Separator";
@@ -263,11 +262,9 @@ export default function CheckoutView({ onAdjustPlan }: CheckoutViewProps) {
           // Empty div to maintain space-between alignment
           <div></div>
         )}
-        <Disabled disabled={isSubmitting}>
-          <Button onClick={handleSubmit}>
-            {isSubmitting ? "Loading..." : "Continue to Payment"}
-          </Button>
-        </Disabled>
+        <Button disabled={isSubmitting} onClick={handleSubmit}>
+          {isSubmitting ? "Loading..." : "Continue to Payment"}
+        </Button>
       </Section>
     </Card>
   );

web/src/app/admin/billing/LicenseActivationCard.tsx

@@ -3,7 +3,6 @@
 import { useState } from "react";
 import Card from "@/refresh-components/cards/Card";
 import { Button } from "@opal/components";
-import { Disabled } from "@opal/core";
 import Text from "@/refresh-components/texts/Text";
 import InputFile from "@/refresh-components/inputs/InputFile";
 import { Section } from "@/layouts/general-layouts";
@@ -147,11 +146,13 @@ export default function LicenseActivationCard({
           <Text headingH3>
             {hasLicense ? "Update License Key" : "Activate License Key"}
           </Text>
-          <Disabled disabled={isActivating}>
-            <Button prominence="secondary" onClick={handleClose}>
-              Cancel
-            </Button>
-          </Disabled>
+          <Button
+            disabled={isActivating}
+            prominence="secondary"
+            onClick={handleClose}
+          >
+            Cancel
+          </Button>
         </Section>
         <Text secondaryBody text03>
           Manually add and activate a license for this Onyx instance.
@@ -221,15 +222,16 @@ export default function LicenseActivationCard({
 
       {/* Footer */}
       <Section flexDirection="row" justifyContent="end" padding={1}>
-        <Disabled disabled={isActivating || !licenseKey.trim() || success}>
-          <Button onClick={handleActivate}>
-            {isActivating
-              ? "Activating..."
-              : hasLicense
-                ? "Update License"
-                : "Activate License"}
-          </Button>
-        </Disabled>
+        <Button
+          disabled={isActivating || !licenseKey.trim() || success}
+          onClick={handleActivate}
+        >
+          {isActivating
+            ? "Activating..."
+            : hasLicense
+              ? "Update License"
+              : "Activate License"}
+        </Button>
       </Section>
     </Card>
   );

web/src/app/admin/billing/PlansView.tsx

@@ -64,7 +64,6 @@ const BUSINESS_FEATURES: PlanFeature[] = [
   { icon: SvgKey, text: "Service Account API Keys" },
   { icon: SvgHardDrive, text: "Self-hosting (Optional)" },
   { icon: SvgPaintBrush, text: "Custom Theming" },
-  { icon: SvgShareWebhook, text: "Hook Extensions" },
 ];
 
 const ENTERPRISE_FEATURES: PlanFeature[] = [
@@ -72,6 +71,7 @@ const ENTERPRISE_FEATURES: PlanFeature[] = [
   { icon: SvgDashboard, text: "Full White-labeling" },
   { icon: SvgUserManage, text: "Custom Roles and Permissions" },
   { icon: SvgSliders, text: "Configurable Usage Limits" },
+  { icon: SvgShareWebhook, text: "Hook Extensions" },
   { icon: SvgServer, text: "Custom Deployments" },
   { icon: SvgGlobe, text: "Region-Specific Data Processing" },
   { icon: SvgHeadsetMic, text: "Enterprise SLAs and Priority Support" },

web/src/app/admin/bots/SlackTokensForm.tsx

@@ -5,7 +5,6 @@ import { Form, Formik } from "formik";
 import * as Yup from "yup";
 import { createSlackBot, updateSlackBot } from "./new/lib";
 import { Button } from "@opal/components";
-import { Disabled } from "@opal/core";
 import Separator from "@/refresh-components/Separator";
 import { useEffect } from "react";
 import { DOCS_ADMINS_PATH } from "@/lib/constants";
@@ -127,16 +126,17 @@ export const SlackTokensForm = ({
             subtext="Optional: User OAuth token for enhanced private channel access"
           />
           <div className="flex justify-end w-full mt-4">
-            <Disabled
+            <Button
               disabled={
                 isSubmitting ||
                 !values.bot_token ||
                 !values.app_token ||
                 !values.name
               }
+              type="submit"
             >
-              <Button type="submit">{isUpdate ? "Update" : "Create"}</Button>
-            </Disabled>
+              {isUpdate ? "Update" : "Create"}
+            </Button>
           </div>
         </Form>
       )}

web/src/app/admin/configuration/llm/ModelConfigurationField.tsx

@@ -6,7 +6,6 @@ import { ManualErrorMessage, TextFormField } from "@/components/Field";
 import { useEffect, useState } from "react";
 import CreateButton from "@/refresh-components/buttons/CreateButton";
 import { Button } from "@opal/components";
-import { Disabled } from "@opal/core";
 import { SvgX } from "@opal/icons";
 import Text from "@/refresh-components/texts/Text";
 
@@ -56,20 +55,17 @@ function ModelConfigurationRow({
         />
       </div>
       <div className="flex flex-col justify-center">
-        <Disabled
+        <Button
           disabled={formikProps.values.model_configurations.length <= 1}
-        >
-          <Button
-            onClick={() => {
-              if (formikProps.values.model_configurations.length > 1) {
-                setError(null);
-                arrayHelpers.remove(index);
-              }
-            }}
-            icon={SvgX}
-            prominence="secondary"
-          />
-        </Disabled>
+          onClick={() => {
+            if (formikProps.values.model_configurations.length > 1) {
+              setError(null);
+              arrayHelpers.remove(index);
+            }
+          }}
+          icon={SvgX}
+          prominence="secondary"
+        />
       </div>
     </div>
   );

web/src/app/admin/connector/[ccPairId]/InlineFileManagement.tsx

@@ -2,7 +2,6 @@
 
 import { useState, useRef } from "react";
 import { Button } from "@opal/components";
-import { Disabled } from "@opal/core";
 import {
   Table,
   TableBody,
@@ -184,25 +183,24 @@ export default function InlineFileManagement({
             </Button>
           ) : (
             <>
-              <Disabled disabled={isSaving}>
-                <Button
-                  prominence="secondary"
-                  onClick={handleCancel}
-                  icon={SvgX}
-                >
-                  Cancel
-                </Button>
-              </Disabled>
-              <Disabled
+              <Button
+                disabled={isSaving}
+                prominence="secondary"
+                onClick={handleCancel}
+                icon={SvgX}
+              >
+                Cancel
+              </Button>
+              <Button
                 disabled={
                   isSaving ||
                   (selectedFilesToRemove.size === 0 && filesToAdd.length === 0)
                 }
+                onClick={handleSaveClick}
+                icon={SvgCheck}
               >
-                <Button onClick={handleSaveClick} icon={SvgCheck}>
-                  {isSaving ? "Saving..." : "Save Changes"}
-                </Button>
-              </Disabled>
+                {isSaving ? "Saving..." : "Save Changes"}
+              </Button>
             </>
           )}
         </div>
@@ -334,15 +332,14 @@ export default function InlineFileManagement({
             className="hidden"
             id={`file-upload-${connectorId}`}
           />
-          <Disabled disabled={isSaving}>
-            <Button
-              prominence="secondary"
-              onClick={() => fileInputRef.current?.click()}
-              icon={SvgPlusCircle}
-            >
-              Add Files
-            </Button>
-          </Disabled>
+          <Button
+            disabled={isSaving}
+            prominence="secondary"
+            onClick={() => fileInputRef.current?.click()}
+            icon={SvgPlusCircle}
+          >
+            Add Files
+          </Button>
         </div>
       )}
 
@@ -398,19 +395,16 @@ export default function InlineFileManagement({
           </Modal.Body>
 
           <Modal.Footer>
-            <Disabled disabled={isSaving}>
-              <Button
-                prominence="secondary"
-                onClick={() => setShowSaveConfirm(false)}
-              >
-                Cancel
-              </Button>
-            </Disabled>
-            <Disabled disabled={isSaving}>
-              <Button onClick={handleConfirmSave}>
-                {isSaving ? "Saving..." : "Confirm & Save"}
-              </Button>
-            </Disabled>
+            <Button
+              disabled={isSaving}
+              prominence="secondary"
+              onClick={() => setShowSaveConfirm(false)}
+            >
+              Cancel
+            </Button>
+            <Button disabled={isSaving} onClick={handleConfirmSave}>
+              {isSaving ? "Saving..." : "Confirm & Save"}
+            </Button>
           </Modal.Footer>
         </Modal.Content>
       </Modal>

web/src/app/admin/connector/[ccPairId]/ReIndexModal.tsx

@@ -1,7 +1,6 @@
 "use client";
 
 import { Button } from "@opal/components";
-import { Disabled } from "@opal/core";
 import { useState } from "react";
 import { toast } from "@/hooks/useToast";
 import { triggerIndexing } from "@/app/admin/connector/[ccPairId]/lib";
@@ -116,9 +115,9 @@ export default function ReIndexModal({ hide, onRunIndex }: ReIndexModalProps) {
             This will pull in and index all documents that have changed and/or
             have been added since the last successful indexing run.
           </Text>
-          <Disabled disabled={isProcessing}>
-            <Button onClick={() => handleRunIndex(false)}>Run Update</Button>
-          </Disabled>
+          <Button disabled={isProcessing} onClick={() => handleRunIndex(false)}>
+            Run Update
+          </Button>
 
           <Separator />
 
@@ -131,11 +130,9 @@ export default function ReIndexModal({ hide, onRunIndex }: ReIndexModalProps) {
             in the source, this may take a long time.
           </Text>
 
-          <Disabled disabled={isProcessing}>
-            <Button onClick={() => handleRunIndex(true)}>
-              Run Complete Re-Indexing
-            </Button>
-          </Disabled>
+          <Button disabled={isProcessing} onClick={() => handleRunIndex(true)}>
+            Run Complete Re-Indexing
+          </Button>
         </Modal.Body>
       </Modal.Content>
     </Modal>

web/src/app/admin/connectors/[connector]/AddConnectorPage.tsx

@@ -56,7 +56,6 @@ import {
 import { CreateStdOAuthCredential } from "@/components/credentials/actions/CreateStdOAuthCredential";
 import { Spinner } from "@/components/Spinner";
 import { Button } from "@opal/components";
-import { Disabled } from "@opal/core";
 import { deleteConnector } from "@/lib/connector";
 import ConnectorDocsLink from "@/components/admin/connectors/ConnectorDocsLink";
 import Text from "@/refresh-components/texts/Text";
@@ -580,19 +579,18 @@ export default function AddConnector({
                       {/* Button to sign in via OAuth */}
                       {oauthSupportedSources.includes(connector) &&
                         (NEXT_PUBLIC_CLOUD_ENABLED || NEXT_PUBLIC_TEST_ENV) && (
-                          <Disabled disabled={isAuthorizing}>
-                            <Button
-                              variant="action"
-                              onClick={handleAuthorize}
-                              hidden={!isAuthorizeVisible}
-                            >
-                              {isAuthorizing
-                                ? "Authorizing..."
-                                : `Authorize with ${getSourceDisplayName(
-                                    connector
-                                  )}`}
-                            </Button>
-                          </Disabled>
+                          <Button
+                            disabled={isAuthorizing}
+                            variant="action"
+                            onClick={handleAuthorize}
+                            hidden={!isAuthorizeVisible}
+                          >
+                            {isAuthorizing
+                              ? "Authorizing..."
+                              : `Authorize with ${getSourceDisplayName(
+                                  connector
+                                )}`}
+                          </Button>
                         )}
                     </div>
                   )}

web/src/app/admin/connectors/[connector]/NavigationRow.tsx

@@ -1,6 +1,5 @@
 import { useFormContext } from "@/components/context/FormContext";
 import { Button } from "@opal/components";
-import { Disabled } from "@opal/core";
 import { SvgArrowLeft, SvgArrowRight, SvgPlusCircle } from "@opal/icons";
 
 const NavigationRow = ({
@@ -34,35 +33,35 @@ const NavigationRow = ({
       </div>
       <div className="flex justify-center">
         {(formStep > 0 || noCredentials) && (
-          <Disabled disabled={!isValid}>
-            <Button rightIcon={SvgPlusCircle} onClick={onSubmit}>
-              Create Connector
-            </Button>
-          </Disabled>
+          <Button
+            disabled={!isValid}
+            rightIcon={SvgPlusCircle}
+            onClick={onSubmit}
+          >
+            Create Connector
+          </Button>
         )}
       </div>
       <div className="flex justify-end">
         {formStep === 0 && (
-          <Disabled disabled={!activatedCredential}>
-            <Button
-              variant="action"
-              rightIcon={SvgArrowRight}
-              onClick={() => nextFormStep()}
-            >
-              Continue
-            </Button>
-          </Disabled>
+          <Button
+            disabled={!activatedCredential}
+            variant="action"
+            rightIcon={SvgArrowRight}
+            onClick={() => nextFormStep()}
+          >
+            Continue
+          </Button>
         )}
         {!noAdvanced && formStep === 1 && (
-          <Disabled disabled={!isValid}>
-            <Button
-              prominence="secondary"
-              rightIcon={SvgArrowRight}
-              onClick={() => nextFormStep()}
-            >
-              Advanced
-            </Button>
-          </Disabled>
+          <Button
+            disabled={!isValid}
+            prominence="secondary"
+            rightIcon={SvgArrowRight}
+            onClick={() => nextFormStep()}
+          >
+            Advanced
+          </Button>
         )}
       </div>
     </div>

web/src/app/admin/connectors/[connector]/oauth/finalize/page.tsx

@@ -4,7 +4,6 @@ import { useEffect, useState } from "react";
 import { usePathname, useRouter, useSearchParams } from "next/navigation";
 import { AdminPageTitle } from "@/components/admin/Title";
 import { Button } from "@opal/components";
-import { Disabled } from "@opal/core";
 import { getSourceMetadata, isValidSource } from "@/lib/sources";
 import { ConfluenceAccessibleResource, ValidSources } from "@/lib/types";
 import CardSection from "@/components/admin/CardSection";
@@ -260,11 +259,9 @@ export default function OAuthFinalizePage() {
                 )}
                 <br />
                 {!redirectUrl && (
-                  <Disabled disabled={!isValid || isSubmitting}>
-                    <Button type="submit">
-                      {isSubmitting ? "Submitting..." : "Submit"}
-                    </Button>
-                  </Disabled>
+                  <Button disabled={!isValid || isSubmitting} type="submit">
+                    {isSubmitting ? "Submitting..." : "Submit"}
+                  </Button>
                 )}
               </Form>
             )}

web/src/app/admin/connectors/[connector]/pages/gdrive/Credential.tsx

@@ -11,7 +11,6 @@ import { TextFormField, SectionHeader } from "@/components/Field";
 import { Form, Formik } from "formik";
 import { User } from "@/lib/types";
 import { Button } from "@opal/components";
-import { Disabled } from "@opal/core";
 import {
   Credential,
   GoogleDriveCredentialJson,
@@ -563,11 +562,9 @@ export const DriveAuthSection = ({
                   subtext="Enter the email of an admin/owner of the Google Organization that owns the Google Drive(s) you want to index."
                 />
                 <div className="flex">
-                  <Disabled disabled={isSubmitting}>
-                    <Button type="submit">
-                      {isSubmitting ? "Creating..." : "Create Credential"}
-                    </Button>
-                  </Disabled>
+                  <Button disabled={isSubmitting} type="submit">
+                    {isSubmitting ? "Creating..." : "Create Credential"}
+                  </Button>
                 </div>
               </Form>
             )}
@@ -587,35 +584,34 @@ export const DriveAuthSection = ({
             Google Drive account.
           </p>
         </div>
-        <Disabled disabled={isAuthenticating}>
-          <Button
-            onClick={async () => {
-              setIsAuthenticating(true);
-              try {
-                const [authUrl, errorMsg] = await setupGoogleDriveOAuth({
-                  isAdmin: true,
-                  name: "OAuth (uploaded)",
-                });
+        <Button
+          disabled={isAuthenticating}
+          onClick={async () => {
+            setIsAuthenticating(true);
+            try {
+              const [authUrl, errorMsg] = await setupGoogleDriveOAuth({
+                isAdmin: true,
+                name: "OAuth (uploaded)",
+              });
 
-                if (authUrl) {
-                  router.push(authUrl as Route);
-                } else {
-                  toast.error(errorMsg);
-                  setIsAuthenticating(false);
-                }
-              } catch (error) {
-                toast.error(
-                  `Failed to authenticate with Google Drive - ${error}`
-                );
+              if (authUrl) {
+                router.push(authUrl as Route);
+              } else {
+                toast.error(errorMsg);
                 setIsAuthenticating(false);
               }
-            }}
-          >
-            {isAuthenticating
-              ? "Authenticating..."
-              : "Authenticate with Google Drive"}
-          </Button>
-        </Disabled>
+            } catch (error) {
+              toast.error(
+                `Failed to authenticate with Google Drive - ${error}`
+              );
+              setIsAuthenticating(false);
+            }
+          }}
+        >
+          {isAuthenticating
+            ? "Authenticating..."
+            : "Authenticate with Google Drive"}
+        </Button>
       </div>
     );
   }

web/src/app/admin/connectors/[connector]/pages/gmail/Credential.tsx

@@ -1,5 +1,4 @@
 import { Button } from "@opal/components";
-import { Disabled } from "@opal/core";
 import { toast } from "@/hooks/useToast";
 import React, { useState, useEffect } from "react";
 import { useSWRConfig } from "swr";
@@ -570,11 +569,9 @@ export const GmailAuthSection = ({
                   subtext="Enter the email of an admin/owner of the Google Organization that owns the Gmail account(s) you want to index."
                 />
                 <div className="flex">
-                  <Disabled disabled={isSubmitting}>
-                    <Button type="submit">
-                      {isSubmitting ? "Creating..." : "Create Credential"}
-                    </Button>
-                  </Disabled>
+                  <Button disabled={isSubmitting} type="submit">
+                    {isSubmitting ? "Creating..." : "Create Credential"}
+                  </Button>
                 </div>
               </Form>
             )}
@@ -593,36 +590,35 @@ export const GmailAuthSection = ({
             read access to the emails you have access to in your Gmail account.
           </p>
         </div>
-        <Disabled disabled={isAuthenticating}>
-          <Button
-            onClick={async () => {
-              setIsAuthenticating(true);
-              try {
-                if (buildMode) {
-                  Cookies.set(CRAFT_OAUTH_COOKIE_NAME, "true", {
-                    path: "/",
-                  });
-                }
-                const [authUrl, errorMsg] = await setupGmailOAuth({
-                  isAdmin: true,
+        <Button
+          disabled={isAuthenticating}
+          onClick={async () => {
+            setIsAuthenticating(true);
+            try {
+              if (buildMode) {
+                Cookies.set(CRAFT_OAUTH_COOKIE_NAME, "true", {
+                  path: "/",
                 });
+              }
+              const [authUrl, errorMsg] = await setupGmailOAuth({
+                isAdmin: true,
+              });
 
-                if (authUrl) {
-                  onOAuthRedirect?.();
-                  router.push(authUrl as Route);
-                } else {
-                  toast.error(errorMsg);
-                  setIsAuthenticating(false);
-                }
-              } catch (error) {
-                toast.error(`Failed to authenticate with Gmail - ${error}`);
+              if (authUrl) {
+                onOAuthRedirect?.();
+                router.push(authUrl as Route);
+              } else {
+                toast.error(errorMsg);
                 setIsAuthenticating(false);
               }
-            }}
-          >
-            {isAuthenticating ? "Authenticating..." : "Authenticate with Gmail"}
-          </Button>
-        </Disabled>
+            } catch (error) {
+              toast.error(`Failed to authenticate with Gmail - ${error}`);
+              setIsAuthenticating(false);
+            }
+          }}
+        >
+          {isAuthenticating ? "Authenticating..." : "Authenticate with Gmail"}
+        </Button>
       </div>
     );
   }