style: align test conventions with existing codebase

- Prefix unused mock params with _ and type as Any
- Extract shared db session mock setup into helper
- Remove unused pytest import
- Use module path constant to reduce repetition

.github/workflows/deployment.yml

@@ -704,6 +704,9 @@ jobs:
             NEXT_PUBLIC_FORGOT_PASSWORD_ENABLED=true
             NEXT_PUBLIC_INCLUDE_ERROR_POPUP_SUPPORT_LINK=true
             NODE_OPTIONS=--max-old-space-size=8192
+            SENTRY_RELEASE=${{ github.sha }}
+          secrets: |
+            sentry_auth_token=${{ secrets.SENTRY_AUTH_TOKEN }}
           cache-from: |
             type=registry,ref=${{ env.RUNS_ON_ECR_CACHE }}:cloudweb-cache-amd64
             type=registry,ref=${{ env.REGISTRY_IMAGE }}:latest
@@ -786,6 +789,9 @@ jobs:
             NEXT_PUBLIC_FORGOT_PASSWORD_ENABLED=true
             NEXT_PUBLIC_INCLUDE_ERROR_POPUP_SUPPORT_LINK=true
             NODE_OPTIONS=--max-old-space-size=8192
+            SENTRY_RELEASE=${{ github.sha }}
+          secrets: |
+            sentry_auth_token=${{ secrets.SENTRY_AUTH_TOKEN }}
           cache-from: |
             type=registry,ref=${{ env.RUNS_ON_ECR_CACHE }}:cloudweb-cache-arm64
             type=registry,ref=${{ env.REGISTRY_IMAGE }}:latest

.github/workflows/nightly-llm-provider-chat.yml

@@ -35,6 +35,7 @@ jobs:
     needs: [provider-chat-test]
     if: failure() && github.event_name == 'schedule'
     runs-on: ubuntu-slim
+    environment: ci-protected
     timeout-minutes: 5
     steps:
       - name: Checkout

.github/workflows/post-merge-beta-cherry-pick.yml

@@ -183,6 +183,7 @@ jobs:
       - cherry-pick-to-latest-release
     if: needs.resolve-cherry-pick-request.outputs.should_cherrypick == 'true' && needs.resolve-cherry-pick-request.result == 'success' && needs.cherry-pick-to-latest-release.result == 'success'
     runs-on: ubuntu-slim
+    environment: ci-protected
     timeout-minutes: 10
     steps:
       - name: Checkout
@@ -232,6 +233,7 @@ jobs:
       - cherry-pick-to-latest-release
     if: always() && needs.resolve-cherry-pick-request.outputs.should_cherrypick == 'true' && (needs.resolve-cherry-pick-request.result == 'failure' || needs.cherry-pick-to-latest-release.result == 'failure')
     runs-on: ubuntu-slim
+    environment: ci-protected
     timeout-minutes: 10
     steps:
       - name: Checkout

.github/workflows/pr-desktop-build.yml

@@ -63,7 +63,7 @@ jobs:
           targets: ${{ matrix.target }}
 
       - name: Cache Cargo registry and build
-        uses: actions/cache@cdf6c1fa76f9f475f3d7449005a359c84ca0f306 # zizmor: ignore[cache-poisoning]
+        uses: actions/cache@668228422ae6a00e4ad889ee87cd7109ec5666a7 # zizmor: ignore[cache-poisoning]
         with:
           path: |
             ~/.cargo/bin/

.github/workflows/pr-helm-chart-testing.yml

@@ -41,7 +41,7 @@ jobs:
           version: v3.19.0
 
       - name: Set up chart-testing
-        uses: helm/chart-testing-action@b5eebdd9998021f29756c53432f48dab66394810
+        uses: helm/chart-testing-action@2e2940618cb426dce2999631d543b53cdcfc8527
         with:
           uv_version: "0.9.9"
 

.github/workflows/pr-playwright-tests.yml

@@ -284,7 +284,7 @@ jobs:
 
       - name: Cache playwright cache
         # zizmor: ignore[cache-poisoning] ephemeral runners; no release artifacts
-        uses: runs-on/cache@50350ad4242587b6c8c2baa2e740b1bc11285ff4 # ratchet:runs-on/cache@v4
+        uses: runs-on/cache@a5f51d6f3fece787d03b7b4e981c82538a0654ed # ratchet:runs-on/cache@v4
         with:
           path: ~/.cache/ms-playwright
           key: ${{ runner.os }}-playwright-npm-${{ hashFiles('web/package-lock.json') }}
@@ -626,7 +626,7 @@ jobs:
 
       - name: Cache playwright cache
         # zizmor: ignore[cache-poisoning] ephemeral runners; no release artifacts
-        uses: runs-on/cache@50350ad4242587b6c8c2baa2e740b1bc11285ff4 # ratchet:runs-on/cache@v4
+        uses: runs-on/cache@a5f51d6f3fece787d03b7b4e981c82538a0654ed # ratchet:runs-on/cache@v4
         with:
           path: ~/.cache/ms-playwright
           key: ${{ runner.os }}-playwright-npm-${{ hashFiles('web/package-lock.json') }}

.github/workflows/pr-python-checks.yml

@@ -56,7 +56,7 @@ jobs:
 
       - name: Cache mypy cache
         if: ${{ vars.DISABLE_MYPY_CACHE != 'true' }}
-        uses: runs-on/cache@50350ad4242587b6c8c2baa2e740b1bc11285ff4 # ratchet:runs-on/cache@v4
+        uses: runs-on/cache@a5f51d6f3fece787d03b7b4e981c82538a0654ed # ratchet:runs-on/cache@v4
         with:
           path: .mypy_cache
           key: mypy-${{ runner.os }}-${{ github.base_ref || github.event.merge_group.base_ref || 'main' }}-${{ hashFiles('**/*.py', '**/*.pyi', 'pyproject.toml') }}

.github/workflows/pr-python-model-tests.yml

@@ -31,6 +31,7 @@ jobs:
       - runner=4cpu-linux-arm64
       - "run-id=${{ github.run_id }}-model-check"
       - "extras=ecr-cache"
+    environment: ci-protected
     timeout-minutes: 45
 
     env:

.github/workflows/preview.yml

@@ -15,6 +15,7 @@ permissions:
 jobs:
   Deploy-Preview:
     runs-on: ubuntu-latest
+    environment: ci-protected
     timeout-minutes: 30
     steps:
       - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd

.github/workflows/storybook-deploy.yml

@@ -25,6 +25,7 @@ permissions:
 jobs:
   Deploy-Storybook:
     runs-on: ubuntu-latest
+    environment: ci-protected
     timeout-minutes: 30
     steps:
       - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # ratchet:actions/checkout@v4
@@ -54,6 +55,7 @@ jobs:
     needs: Deploy-Storybook
     if: always() && needs.Deploy-Storybook.result == 'failure'
     runs-on: ubuntu-latest
+    environment: ci-protected
     timeout-minutes: 10
     steps:
       - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # ratchet:actions/checkout@v4

.github/workflows/sync_foss.yml

@@ -9,6 +9,7 @@ on:
 jobs:
   sync-foss:
     runs-on: ubuntu-latest
+    environment: ci-protected
     timeout-minutes: 45
     permissions:
       contents: read

.github/workflows/tag-nightly.yml

@@ -11,6 +11,7 @@ permissions:
 jobs:
   create-and-push-tag:
     runs-on: ubuntu-slim
+    environment: ci-protected
     timeout-minutes: 45
 
     steps:

backend/ee/onyx/background/celery/tasks/tenant_provisioning/tasks.py

@@ -13,6 +13,7 @@ from redis.lock import Lock as RedisLock
 from ee.onyx.server.tenants.provisioning import setup_tenant
 from ee.onyx.server.tenants.schema_management import create_schema_if_not_exists
 from ee.onyx.server.tenants.schema_management import get_current_alembic_version
+from ee.onyx.server.tenants.schema_management import run_alembic_migrations
 from onyx.background.celery.apps.app_base import task_logger
 from onyx.configs.app_configs import TARGET_AVAILABLE_TENANTS
 from onyx.configs.constants import ONYX_CLOUD_TENANT_ID
@@ -29,9 +30,10 @@ from shared_configs.configs import TENANT_ID_PREFIX
 # Each tenant takes ~80s (alembic migrations), so 5 tenants ≈ 7 minutes.
 _MAX_TENANTS_PER_RUN = 5
 
-# Time limits sized for worst-case batch: _MAX_TENANTS_PER_RUN × ~90s + buffer.
-_TENANT_PROVISIONING_SOFT_TIME_LIMIT = 60 * 10  # 10 minutes
-_TENANT_PROVISIONING_TIME_LIMIT = 60 * 15  # 15 minutes
+# Time limits sized for worst-case: provisioning up to _MAX_TENANTS_PER_RUN new tenants
+# (~90s each) plus migrating up to TARGET_AVAILABLE_TENANTS pool tenants (~90s each).
+_TENANT_PROVISIONING_SOFT_TIME_LIMIT = 60 * 20  # 20 minutes
+_TENANT_PROVISIONING_TIME_LIMIT = 60 * 25  # 25 minutes
 
 
 @shared_task(
@@ -91,8 +93,7 @@ def check_available_tenants(self: Task) -> None:  # noqa: ARG001
         batch_size = min(tenants_to_provision, _MAX_TENANTS_PER_RUN)
         if batch_size < tenants_to_provision:
             task_logger.info(
-                f"Capping batch to {batch_size} "
-                f"(need {tenants_to_provision}, will catch up next cycle)"
+                f"Capping batch to {batch_size} (need {tenants_to_provision}, will catch up next cycle)"
             )
 
         provisioned = 0
@@ -103,12 +104,14 @@ def check_available_tenants(self: Task) -> None:  # noqa: ARG001
                     provisioned += 1
             except Exception:
                 task_logger.exception(
-                    f"Failed to provision tenant {i + 1}/{batch_size}, "
-                    "continuing with remaining tenants"
+                    f"Failed to provision tenant {i + 1}/{batch_size}, continuing with remaining tenants"
                 )
 
         task_logger.info(f"Provisioning complete: {provisioned}/{batch_size} succeeded")
 
+        # Migrate any pool tenants that were provisioned before a new migration was deployed
+        _migrate_stale_pool_tenants()
+
     except Exception:
         task_logger.exception("Error in check_available_tenants task")
 
@@ -121,6 +124,46 @@ def check_available_tenants(self: Task) -> None:  # noqa: ARG001
             )
 
 
+def _migrate_stale_pool_tenants() -> None:
+    """
+    Run alembic upgrade head on all pool tenants. Since alembic upgrade head is
+    idempotent, tenants already at head are a fast no-op. This ensures pool
+    tenants are always current so that signup doesn't hit schema mismatches
+    (e.g. missing columns added after the tenant was pre-provisioned).
+    """
+    with get_session_with_shared_schema() as db_session:
+        pool_tenants = db_session.query(AvailableTenant).all()
+        tenant_ids = [t.tenant_id for t in pool_tenants]
+
+    if not tenant_ids:
+        return
+
+    task_logger.info(
+        f"Checking {len(tenant_ids)} pool tenant(s) for pending migrations"
+    )
+
+    for tenant_id in tenant_ids:
+        try:
+            run_alembic_migrations(tenant_id)
+            new_version = get_current_alembic_version(tenant_id)
+            with get_session_with_shared_schema() as db_session:
+                tenant = (
+                    db_session.query(AvailableTenant)
+                    .filter_by(tenant_id=tenant_id)
+                    .first()
+                )
+                if tenant and tenant.alembic_version != new_version:
+                    task_logger.info(
+                        f"Migrated pool tenant {tenant_id}: {tenant.alembic_version} -> {new_version}"
+                    )
+                    tenant.alembic_version = new_version
+                    db_session.commit()
+        except Exception:
+            task_logger.exception(
+                f"Failed to migrate pool tenant {tenant_id}, skipping"
+            )
+
+
 def pre_provision_tenant() -> bool:
     """
     Pre-provision a new tenant and store it in the NewAvailableTenant table.

backend/ee/onyx/background/celery/tasks/ttl_management/tasks.py

@@ -54,27 +54,35 @@ def perform_ttl_management_task(
                 retention_limit_days, db_session
             )
 
+        failures = 0
         for user_id, session_id in old_chat_sessions:
-            # one session per delete so that we don't blow up if a deletion fails.
-            with get_session_with_current_tenant() as db_session:
-                delete_chat_session(
-                    user_id,
-                    session_id,
-                    db_session,
-                    include_deleted=True,
-                    hard_delete=True,
+            try:
+                with get_session_with_current_tenant() as db_session:
+                    delete_chat_session(
+                        user_id,
+                        session_id,
+                        db_session,
+                        include_deleted=True,
+                        hard_delete=True,
+                    )
+            except Exception:
+                failures += 1
+                logger.exception(
+                    "Failed to delete chat session "
+                    f"user_id={user_id} session_id={session_id}, "
+                    "continuing with remaining sessions"
                 )
 
         with get_session_with_current_tenant() as db_session:
             mark_task_as_finished_with_id(
                 db_session=db_session,
                 task_id=task_id,
-                success=True,
+                success=failures == 0,
             )
 
     except Exception:
         logger.exception(
-            f"delete_chat_session exceptioned. user_id={user_id} session_id={session_id}"
+            f"TTL management task failed. user_id={user_id} session_id={session_id}"
         )
         with get_session_with_current_tenant() as db_session:
             mark_task_as_finished_with_id(

backend/ee/onyx/server/tenants/provisioning.py

@@ -99,6 +99,26 @@ async def get_or_provision_tenant(
         tenant_id = await get_available_tenant()
 
         if tenant_id:
+            # Run migrations to ensure the pre-provisioned tenant schema is current.
+            # Pool tenants may have been created before a new migration was deployed.
+            # Capture as a non-optional local so mypy can type the lambda correctly.
+            _tenant_id: str = tenant_id
+            loop = asyncio.get_running_loop()
+            try:
+                await loop.run_in_executor(
+                    None, lambda: run_alembic_migrations(_tenant_id)
+                )
+            except Exception:
+                # The tenant was already dequeued from the pool — roll it back so
+                # it doesn't end up orphaned (schema exists, but not assigned to anyone).
+                logger.exception(
+                    f"Migration failed for pre-provisioned tenant {_tenant_id}; rolling back"
+                )
+                try:
+                    await rollback_tenant_provisioning(_tenant_id)
+                except Exception:
+                    logger.exception(f"Failed to rollback orphaned tenant {_tenant_id}")
+                raise
             # If we have a pre-provisioned tenant, assign it to the user
             await assign_tenant_to_user(tenant_id, email, referral_source)
             logger.info(f"Assigned pre-provisioned tenant {tenant_id} to user {email}")

backend/model_server/main.py

@@ -100,6 +100,7 @@ def get_model_app() -> FastAPI:
             dsn=SENTRY_DSN,
             integrations=[StarletteIntegration(), FastApiIntegration()],
             traces_sample_rate=0.1,
+            release=__version__,
         )
         logger.info("Sentry initialized")
     else:

backend/onyx/background/celery/apps/app_base.py

@@ -20,6 +20,7 @@ from sentry_sdk.integrations.celery import CeleryIntegration
 from sqlalchemy import text
 from sqlalchemy.orm import Session
 
+from onyx import __version__
 from onyx.background.celery.apps.task_formatters import CeleryTaskColoredFormatter
 from onyx.background.celery.apps.task_formatters import CeleryTaskPlainFormatter
 from onyx.background.celery.celery_utils import celery_is_worker_primary
@@ -65,6 +66,7 @@ if SENTRY_DSN:
         dsn=SENTRY_DSN,
         integrations=[CeleryIntegration()],
         traces_sample_rate=0.1,
+        release=__version__,
     )
     logger.info("Sentry initialized")
 else:
@@ -515,7 +517,8 @@ def reset_tenant_id(
 
 
 def wait_for_vespa_or_shutdown(
-    sender: Any, **kwargs: Any  # noqa: ARG001
+    sender: Any,  # noqa: ARG001
+    **kwargs: Any,  # noqa: ARG001
 ) -> None:  # noqa: ARG001
     """Waits for Vespa to become ready subject to a timeout.
     Raises WorkerShutdown if the timeout is reached."""

backend/onyx/background/celery/tasks/docfetching/tasks.py

@@ -9,6 +9,7 @@ from celery import Celery
 from celery import shared_task
 from celery import Task
 
+from onyx import __version__
 from onyx.background.celery.apps.app_base import task_logger
 from onyx.background.celery.memory_monitoring import emit_process_memory
 from onyx.background.celery.tasks.docprocessing.heartbeat import start_heartbeat
@@ -137,6 +138,7 @@ def _docfetching_task(
         sentry_sdk.init(
             dsn=SENTRY_DSN,
             traces_sample_rate=0.1,
+            release=__version__,
         )
         logger.info("Sentry initialized")
     else:

backend/onyx/configs/app_configs.py

@@ -805,6 +805,10 @@ MINI_CHUNK_SIZE = 150
 # This is the number of regular chunks per large chunk
 LARGE_CHUNK_RATIO = 4
 
+# The maximum number of chunks that can be held for 1 document processing batch
+# The purpose of this is to set an upper bound on memory usage
+MAX_CHUNKS_PER_DOC_BATCH = int(os.environ.get("MAX_CHUNKS_PER_DOC_BATCH") or 1000)
+
 # Include the document level metadata in each chunk. If the metadata is too long, then it is thrown out
 # We don't want the metadata to overwhelm the actual contents of the chunk
 SKIP_METADATA_IN_CHUNK = os.environ.get("SKIP_METADATA_IN_CHUNK", "").lower() == "true"

backend/onyx/configs/constants.py

@@ -212,6 +212,7 @@ class DocumentSource(str, Enum):
     PRODUCTBOARD = "productboard"
     FILE = "file"
     CODA = "coda"
+    CANVAS = "canvas"
     NOTION = "notion"
     ZULIP = "zulip"
     LINEAR = "linear"
@@ -672,6 +673,7 @@ DocumentSourceDescription: dict[DocumentSource, str] = {
     DocumentSource.SLAB: "slab data",
     DocumentSource.PRODUCTBOARD: "productboard data (boards, etc.)",
     DocumentSource.FILE: "files",
+    DocumentSource.CANVAS: "canvas lms - courses, pages, assignments, and announcements",
     DocumentSource.CODA: "coda - team workspace with docs, tables, and pages",
     DocumentSource.NOTION: "notion data - a workspace that combines note-taking, \
 project management, and collaboration tools into a single, customizable platform",

backend/onyx/connectors/canvas/access.py

@@ -0,0 +1,32 @@
+"""
+Permissioning / AccessControl logic for Canvas courses.
+
+CE stub — returns None (no permissions). The EE implementation is loaded
+at runtime via ``fetch_versioned_implementation``.
+"""
+
+from collections.abc import Callable
+from typing import cast
+
+from onyx.access.models import ExternalAccess
+from onyx.connectors.canvas.client import CanvasApiClient
+from onyx.utils.variable_functionality import fetch_versioned_implementation
+from onyx.utils.variable_functionality import global_version
+
+
+def get_course_permissions(
+    canvas_client: CanvasApiClient,
+    course_id: int,
+) -> ExternalAccess | None:
+    if not global_version.is_ee_version():
+        return None
+
+    ee_get_course_permissions = cast(
+        Callable[[CanvasApiClient, int], ExternalAccess | None],
+        fetch_versioned_implementation(
+            "onyx.external_permissions.canvas.access",
+            "get_course_permissions",
+        ),
+    )
+
+    return ee_get_course_permissions(canvas_client, course_id)

backend/onyx/connectors/canvas/client.py

@@ -2,6 +2,7 @@ from __future__ import annotations
 
 import logging
 import re
+from collections.abc import Iterator
 from typing import Any
 from urllib.parse import urlparse
 
@@ -190,3 +191,22 @@ class CanvasApiClient:
         if clean_endpoint:
             final_url += "/" + clean_endpoint
         return final_url
+
+    def paginate(
+        self,
+        endpoint: str,
+        params: dict[str, Any] | None = None,
+    ) -> Iterator[list[Any]]:
+        """Yield each page of results, following Link-header pagination.
+
+        Makes the first request with endpoint + params, then follows
+        next_url from Link headers for subsequent pages.
+        """
+        response, next_url = self.get(endpoint, params=params)
+        while True:
+            if not response:
+                break
+            yield response
+            if not next_url:
+                break
+            response, next_url = self.get(full_url=next_url)

backend/onyx/connectors/canvas/connector.py

@@ -1,17 +1,82 @@
+from datetime import datetime
+from datetime import timezone
+from typing import Any
+from typing import cast
 from typing import Literal
+from typing import NoReturn
 from typing import TypeAlias
 
 from pydantic import BaseModel
+from retry import retry
+from typing_extensions import override
 
+from onyx.access.models import ExternalAccess
+from onyx.configs.app_configs import INDEX_BATCH_SIZE
+from onyx.configs.constants import DocumentSource
+from onyx.connectors.canvas.access import get_course_permissions
+from onyx.connectors.canvas.client import CanvasApiClient
+from onyx.connectors.exceptions import ConnectorValidationError
+from onyx.connectors.exceptions import CredentialExpiredError
+from onyx.connectors.exceptions import InsufficientPermissionsError
+from onyx.connectors.exceptions import UnexpectedValidationError
+from onyx.connectors.interfaces import CheckpointedConnectorWithPermSync
+from onyx.connectors.interfaces import CheckpointOutput
+from onyx.connectors.interfaces import GenerateSlimDocumentOutput
+from onyx.connectors.interfaces import SecondsSinceUnixEpoch
+from onyx.connectors.interfaces import SlimConnectorWithPermSync
 from onyx.connectors.models import ConnectorCheckpoint
+from onyx.connectors.models import ConnectorMissingCredentialError
+from onyx.connectors.models import Document
+from onyx.connectors.models import ImageSection
+from onyx.connectors.models import TextSection
+from onyx.error_handling.exceptions import OnyxError
+from onyx.file_processing.html_utils import parse_html_page_basic
+from onyx.indexing.indexing_heartbeat import IndexingHeartbeatInterface
+from onyx.utils.logger import setup_logger
+
+logger = setup_logger()
+
+
+def _handle_canvas_api_error(e: OnyxError) -> NoReturn:
+    """Map Canvas API errors to connector framework exceptions."""
+    if e.status_code == 401:
+        raise CredentialExpiredError(
+            "Canvas API token is invalid or expired (HTTP 401)."
+        )
+    elif e.status_code == 403:
+        raise InsufficientPermissionsError(
+            "Canvas API token does not have sufficient permissions (HTTP 403)."
+        )
+    elif e.status_code == 429:
+        raise ConnectorValidationError(
+            "Canvas rate-limit exceeded (HTTP 429). Please try again later."
+        )
+    elif e.status_code >= 500:
+        raise UnexpectedValidationError(
+            f"Unexpected Canvas HTTP error (status={e.status_code}): {e}"
+        )
+    else:
+        raise ConnectorValidationError(
+            f"Canvas API error (status={e.status_code}): {e}"
+        )
 
 
 class CanvasCourse(BaseModel):
     id: int
-    name: str
-    course_code: str
-    created_at: str
-    workflow_state: str
+    name: str | None = None
+    course_code: str | None = None
+    created_at: str | None = None
+    workflow_state: str | None = None
+
+    @classmethod
+    def from_api(cls, payload: dict[str, Any]) -> "CanvasCourse":
+        return cls(
+            id=payload["id"],
+            name=payload.get("name"),
+            course_code=payload.get("course_code"),
+            created_at=payload.get("created_at"),
+            workflow_state=payload.get("workflow_state"),
+        )
 
 
 class CanvasPage(BaseModel):
@@ -19,10 +84,22 @@ class CanvasPage(BaseModel):
     url: str
     title: str
     body: str | None = None
-    created_at: str
-    updated_at: str
+    created_at: str | None = None
+    updated_at: str | None = None
     course_id: int
 
+    @classmethod
+    def from_api(cls, payload: dict[str, Any], course_id: int) -> "CanvasPage":
+        return cls(
+            page_id=payload["page_id"],
+            url=payload["url"],
+            title=payload["title"],
+            body=payload.get("body"),
+            created_at=payload.get("created_at"),
+            updated_at=payload.get("updated_at"),
+            course_id=course_id,
+        )
+
 
 class CanvasAssignment(BaseModel):
     id: int
@@ -30,10 +107,23 @@ class CanvasAssignment(BaseModel):
     description: str | None = None
     html_url: str
     course_id: int
-    created_at: str
-    updated_at: str
+    created_at: str | None = None
+    updated_at: str | None = None
     due_at: str | None = None
 
+    @classmethod
+    def from_api(cls, payload: dict[str, Any], course_id: int) -> "CanvasAssignment":
+        return cls(
+            id=payload["id"],
+            name=payload["name"],
+            description=payload.get("description"),
+            html_url=payload["html_url"],
+            course_id=course_id,
+            created_at=payload.get("created_at"),
+            updated_at=payload.get("updated_at"),
+            due_at=payload.get("due_at"),
+        )
+
 
 class CanvasAnnouncement(BaseModel):
     id: int
@@ -43,6 +133,17 @@ class CanvasAnnouncement(BaseModel):
     posted_at: str | None = None
     course_id: int
 
+    @classmethod
+    def from_api(cls, payload: dict[str, Any], course_id: int) -> "CanvasAnnouncement":
+        return cls(
+            id=payload["id"],
+            title=payload["title"],
+            message=payload.get("message"),
+            html_url=payload["html_url"],
+            posted_at=payload.get("posted_at"),
+            course_id=course_id,
+        )
+
 
 CanvasStage: TypeAlias = Literal["pages", "assignments", "announcements"]
 
@@ -72,3 +173,286 @@ class CanvasConnectorCheckpoint(ConnectorCheckpoint):
         self.current_course_index += 1
         self.stage = "pages"
         self.next_url = None
+
+
+class CanvasConnector(
+    CheckpointedConnectorWithPermSync[CanvasConnectorCheckpoint],
+    SlimConnectorWithPermSync,
+):
+    def __init__(
+        self,
+        canvas_base_url: str,
+        batch_size: int = INDEX_BATCH_SIZE,
+    ) -> None:
+        self.canvas_base_url = canvas_base_url.rstrip("/").removesuffix("/api/v1")
+        self.batch_size = batch_size
+        self._canvas_client: CanvasApiClient | None = None
+        self._course_permissions_cache: dict[int, ExternalAccess | None] = {}
+
+    @property
+    def canvas_client(self) -> CanvasApiClient:
+        if self._canvas_client is None:
+            raise ConnectorMissingCredentialError("Canvas")
+        return self._canvas_client
+
+    def _get_course_permissions(self, course_id: int) -> ExternalAccess | None:
+        """Get course permissions with caching."""
+        if course_id not in self._course_permissions_cache:
+            self._course_permissions_cache[course_id] = get_course_permissions(
+                canvas_client=self.canvas_client,
+                course_id=course_id,
+            )
+        return self._course_permissions_cache[course_id]
+
+    @retry(tries=3, delay=1, backoff=2)
+    def _list_courses(self) -> list[CanvasCourse]:
+        """Fetch all courses accessible to the authenticated user."""
+        logger.debug("Fetching Canvas courses")
+
+        courses: list[CanvasCourse] = []
+        for page in self.canvas_client.paginate(
+            "courses", params={"per_page": "100", "state[]": "available"}
+        ):
+            courses.extend(CanvasCourse.from_api(c) for c in page)
+        return courses
+
+    @retry(tries=3, delay=1, backoff=2)
+    def _list_pages(self, course_id: int) -> list[CanvasPage]:
+        """Fetch all pages for a given course."""
+        logger.debug(f"Fetching pages for course {course_id}")
+
+        pages: list[CanvasPage] = []
+        for page in self.canvas_client.paginate(
+            f"courses/{course_id}/pages",
+            params={"per_page": "100", "include[]": "body", "published": "true"},
+        ):
+            pages.extend(CanvasPage.from_api(p, course_id=course_id) for p in page)
+        return pages
+
+    @retry(tries=3, delay=1, backoff=2)
+    def _list_assignments(self, course_id: int) -> list[CanvasAssignment]:
+        """Fetch all assignments for a given course."""
+        logger.debug(f"Fetching assignments for course {course_id}")
+
+        assignments: list[CanvasAssignment] = []
+        for page in self.canvas_client.paginate(
+            f"courses/{course_id}/assignments",
+            params={"per_page": "100", "published": "true"},
+        ):
+            assignments.extend(
+                CanvasAssignment.from_api(a, course_id=course_id) for a in page
+            )
+        return assignments
+
+    @retry(tries=3, delay=1, backoff=2)
+    def _list_announcements(self, course_id: int) -> list[CanvasAnnouncement]:
+        """Fetch all announcements for a given course."""
+        logger.debug(f"Fetching announcements for course {course_id}")
+
+        announcements: list[CanvasAnnouncement] = []
+        for page in self.canvas_client.paginate(
+            "announcements",
+            params={
+                "per_page": "100",
+                "context_codes[]": f"course_{course_id}",
+                "active_only": "true",
+            },
+        ):
+            announcements.extend(
+                CanvasAnnouncement.from_api(a, course_id=course_id) for a in page
+            )
+        return announcements
+
+    def _build_document(
+        self,
+        doc_id: str,
+        link: str,
+        text: str,
+        semantic_identifier: str,
+        doc_updated_at: datetime | None,
+        course_id: int,
+        doc_type: str,
+    ) -> Document:
+        """Build a Document with standard Canvas fields."""
+        return Document(
+            id=doc_id,
+            sections=cast(
+                list[TextSection | ImageSection],
+                [TextSection(link=link, text=text)],
+            ),
+            source=DocumentSource.CANVAS,
+            semantic_identifier=semantic_identifier,
+            doc_updated_at=doc_updated_at,
+            metadata={"course_id": str(course_id), "type": doc_type},
+        )
+
+    def _convert_page_to_document(self, page: CanvasPage) -> Document:
+        """Convert a Canvas page to a Document."""
+        link = f"{self.canvas_base_url}/courses/{page.course_id}/pages/{page.url}"
+
+        text_parts = [page.title]
+        body_text = parse_html_page_basic(page.body) if page.body else ""
+        if body_text:
+            text_parts.append(body_text)
+
+        doc_updated_at = (
+            datetime.fromisoformat(page.updated_at.replace("Z", "+00:00")).astimezone(
+                timezone.utc
+            )
+            if page.updated_at
+            else None
+        )
+
+        document = self._build_document(
+            doc_id=f"canvas-page-{page.course_id}-{page.page_id}",
+            link=link,
+            text="\n\n".join(text_parts),
+            semantic_identifier=page.title or f"Page {page.page_id}",
+            doc_updated_at=doc_updated_at,
+            course_id=page.course_id,
+            doc_type="page",
+        )
+        return document
+
+    def _convert_assignment_to_document(self, assignment: CanvasAssignment) -> Document:
+        """Convert a Canvas assignment to a Document."""
+        text_parts = [assignment.name]
+        desc_text = (
+            parse_html_page_basic(assignment.description)
+            if assignment.description
+            else ""
+        )
+        if desc_text:
+            text_parts.append(desc_text)
+        if assignment.due_at:
+            due_dt = datetime.fromisoformat(
+                assignment.due_at.replace("Z", "+00:00")
+            ).astimezone(timezone.utc)
+            text_parts.append(f"Due: {due_dt.strftime('%B %d, %Y %H:%M UTC')}")
+
+        doc_updated_at = (
+            datetime.fromisoformat(
+                assignment.updated_at.replace("Z", "+00:00")
+            ).astimezone(timezone.utc)
+            if assignment.updated_at
+            else None
+        )
+
+        document = self._build_document(
+            doc_id=f"canvas-assignment-{assignment.course_id}-{assignment.id}",
+            link=assignment.html_url,
+            text="\n\n".join(text_parts),
+            semantic_identifier=assignment.name or f"Assignment {assignment.id}",
+            doc_updated_at=doc_updated_at,
+            course_id=assignment.course_id,
+            doc_type="assignment",
+        )
+        return document
+
+    def _convert_announcement_to_document(
+        self, announcement: CanvasAnnouncement
+    ) -> Document:
+        """Convert a Canvas announcement to a Document."""
+        text_parts = [announcement.title]
+        msg_text = (
+            parse_html_page_basic(announcement.message) if announcement.message else ""
+        )
+        if msg_text:
+            text_parts.append(msg_text)
+
+        doc_updated_at = (
+            datetime.fromisoformat(
+                announcement.posted_at.replace("Z", "+00:00")
+            ).astimezone(timezone.utc)
+            if announcement.posted_at
+            else None
+        )
+
+        document = self._build_document(
+            doc_id=f"canvas-announcement-{announcement.course_id}-{announcement.id}",
+            link=announcement.html_url,
+            text="\n\n".join(text_parts),
+            semantic_identifier=announcement.title or f"Announcement {announcement.id}",
+            doc_updated_at=doc_updated_at,
+            course_id=announcement.course_id,
+            doc_type="announcement",
+        )
+        return document
+
+    @override
+    def load_credentials(self, credentials: dict[str, Any]) -> dict[str, Any] | None:
+        """Load and validate Canvas credentials."""
+        access_token = credentials.get("canvas_access_token")
+        if not access_token:
+            raise ConnectorMissingCredentialError("Canvas")
+
+        try:
+            client = CanvasApiClient(
+                bearer_token=access_token,
+                canvas_base_url=self.canvas_base_url,
+            )
+            client.get("courses", params={"per_page": "1"})
+        except ValueError as e:
+            raise ConnectorValidationError(f"Invalid Canvas base URL: {e}")
+        except OnyxError as e:
+            _handle_canvas_api_error(e)
+
+        self._canvas_client = client
+        return None
+
+    @override
+    def validate_connector_settings(self) -> None:
+        """Validate Canvas connector settings by testing API access."""
+        try:
+            self.canvas_client.get("courses", params={"per_page": "1"})
+            logger.info("Canvas connector settings validated successfully")
+        except OnyxError as e:
+            _handle_canvas_api_error(e)
+        except ConnectorMissingCredentialError:
+            raise
+        except Exception as exc:
+            raise UnexpectedValidationError(
+                f"Unexpected error during Canvas settings validation: {exc}"
+            )
+
+    @override
+    def load_from_checkpoint(
+        self,
+        start: SecondsSinceUnixEpoch,
+        end: SecondsSinceUnixEpoch,
+        checkpoint: CanvasConnectorCheckpoint,
+    ) -> CheckpointOutput[CanvasConnectorCheckpoint]:
+        # TODO(benwu408): implemented in PR3 (checkpoint)
+        raise NotImplementedError
+
+    @override
+    def load_from_checkpoint_with_perm_sync(
+        self,
+        start: SecondsSinceUnixEpoch,
+        end: SecondsSinceUnixEpoch,
+        checkpoint: CanvasConnectorCheckpoint,
+    ) -> CheckpointOutput[CanvasConnectorCheckpoint]:
+        # TODO(benwu408): implemented in PR3 (checkpoint)
+        raise NotImplementedError
+
+    @override
+    def build_dummy_checkpoint(self) -> CanvasConnectorCheckpoint:
+        # TODO(benwu408): implemented in PR3 (checkpoint)
+        raise NotImplementedError
+
+    @override
+    def validate_checkpoint_json(
+        self, checkpoint_json: str
+    ) -> CanvasConnectorCheckpoint:
+        # TODO(benwu408): implemented in PR3 (checkpoint)
+        raise NotImplementedError
+
+    @override
+    def retrieve_all_slim_docs_perm_sync(
+        self,
+        start: SecondsSinceUnixEpoch | None = None,
+        end: SecondsSinceUnixEpoch | None = None,
+        callback: IndexingHeartbeatInterface | None = None,
+    ) -> GenerateSlimDocumentOutput:
+        # TODO(benwu408): implemented in PR4 (perm sync)
+        raise NotImplementedError

backend/onyx/connectors/registry.py

@@ -72,6 +72,10 @@ CONNECTOR_CLASS_MAP = {
         module_path="onyx.connectors.coda.connector",
         class_name="CodaConnector",
     ),
+    DocumentSource.CANVAS: ConnectorMapping(
+        module_path="onyx.connectors.canvas.connector",
+        class_name="CanvasConnector",
+    ),
     DocumentSource.NOTION: ConnectorMapping(
         module_path="onyx.connectors.notion.connector",
         class_name="NotionConnector",

backend/onyx/db/chat.py

@@ -185,7 +185,15 @@ def delete_messages_and_files_from_chat_session(
     for _, files in messages_with_files:
         file_store = get_default_file_store()
         for file_info in files or []:
-            file_store.delete_file(file_id=file_info.get("id"))
+            try:
+                file_store.delete_file(file_id=file_info.get("id"))
+            except Exception:
+                logger.warning(
+                    "Failed to delete file %s from file store during "
+                    "chat session cleanup, skipping.",
+                    file_info.get("id"),
+                )
+                continue
 
     # Delete ChatMessage records - CASCADE constraints will automatically handle:
     # - ChatMessage__StandardAnswer relationship records

backend/onyx/document_index/opensearch/opensearch_document_index.py

@@ -6,6 +6,7 @@ import httpx
 from opensearchpy import NotFoundError
 
 from onyx.access.models import DocumentAccess
+from onyx.configs.app_configs import MAX_CHUNKS_PER_DOC_BATCH
 from onyx.configs.app_configs import VERIFY_CREATE_OPENSEARCH_INDEX_ON_INIT_MT
 from onyx.configs.chat_configs import NUM_RETURNED_HITS
 from onyx.configs.chat_configs import TITLE_CONTENT_RATIO
@@ -738,6 +739,9 @@ class OpenSearchDocumentIndex(DocumentIndex):
                     _flush_chunks(current_chunks)
                 current_doc_id = doc_id
                 current_chunks = [chunk]
+            elif len(current_chunks) >= MAX_CHUNKS_PER_DOC_BATCH:
+                _flush_chunks(current_chunks)
+                current_chunks = [chunk]
             else:
                 current_chunks.append(chunk)
 

backend/onyx/document_index/vespa/vespa_document_index.py

@@ -10,6 +10,7 @@ import httpx
 from pydantic import BaseModel
 from retry import retry
 
+from onyx.configs.app_configs import MAX_CHUNKS_PER_DOC_BATCH
 from onyx.configs.app_configs import RECENCY_BIAS_MULTIPLIER
 from onyx.configs.app_configs import RERANK_COUNT
 from onyx.configs.chat_configs import DOC_TIME_DECAY
@@ -427,7 +428,9 @@ class VespaDocumentIndex(DocumentIndex):
                 new_document_id_to_original_document_id,
                 all_cleaned_doc_ids,
             )
-            for chunk_batch in batch_generator(cleaned_chunks, BATCH_SIZE):
+            for chunk_batch in batch_generator(
+                cleaned_chunks, min(BATCH_SIZE, MAX_CHUNKS_PER_DOC_BATCH)
+            ):
                 batch_index_vespa_chunks(
                     chunks=chunk_batch,
                     index_name=self._index_name,

backend/onyx/file_processing/extract_file_text.py

@@ -44,6 +44,7 @@ KNOWN_OPENPYXL_BUGS = [
     "Value must be either numerical or a string containing a wildcard",
     "File contains no valid workbook part",
     "Unable to read workbook: could not read stylesheet from None",
+    "Colors must be aRGB hex values",
 ]
 
 

backend/onyx/indexing/adapters/document_indexing_adapter.py

@@ -19,7 +19,8 @@ from onyx.db.document import update_docs_updated_at__no_commit
 from onyx.db.document_set import fetch_document_sets_for_documents
 from onyx.indexing.indexing_pipeline import DocumentBatchPrepareContext
 from onyx.indexing.indexing_pipeline import index_doc_batch_prepare
-from onyx.indexing.models import BuildMetadataAwareChunksResult
+from onyx.indexing.models import ChunkEnrichmentContext
+from onyx.indexing.models import DocAwareChunk
 from onyx.indexing.models import DocMetadataAwareIndexChunk
 from onyx.indexing.models import IndexChunk
 from onyx.indexing.models import UpdatableChunkData
@@ -85,14 +86,21 @@ class DocumentIndexingBatchAdapter:
         ) as transaction:
             yield transaction
 
-    def build_metadata_aware_chunks(
+    def prepare_enrichment(
         self,
-        chunks_with_embeddings: list[IndexChunk],
-        chunk_content_scores: list[float],
-        tenant_id: str,
         context: DocumentBatchPrepareContext,
-    ) -> BuildMetadataAwareChunksResult:
-        """Enrich chunks with access, document sets, boosts, token counts, and hierarchy."""
+        tenant_id: str,
+        chunks: list[DocAwareChunk],
+    ) -> "DocumentChunkEnricher":
+        """Do all DB lookups once and return a per-chunk enricher."""
+        updatable_ids = [doc.id for doc in context.updatable_docs]
+
+        doc_id_to_new_chunk_cnt: dict[str, int] = {
+            doc_id: 0 for doc_id in updatable_ids
+        }
+        for chunk in chunks:
+            if chunk.source_document.id in doc_id_to_new_chunk_cnt:
+                doc_id_to_new_chunk_cnt[chunk.source_document.id] += 1
 
         no_access = DocumentAccess.build(
             user_emails=[],
@@ -102,67 +110,30 @@ class DocumentIndexingBatchAdapter:
             is_public=False,
         )
 
-        updatable_ids = [doc.id for doc in context.updatable_docs]
-
-        doc_id_to_access_info = get_access_for_documents(
-            document_ids=updatable_ids, db_session=self.db_session
-        )
-        doc_id_to_document_set = {
-            document_id: document_sets
-            for document_id, document_sets in fetch_document_sets_for_documents(
+        return DocumentChunkEnricher(
+            doc_id_to_access_info=get_access_for_documents(
                 document_ids=updatable_ids, db_session=self.db_session
-            )
-        }
-
-        doc_id_to_previous_chunk_cnt: dict[str, int] = {
-            document_id: chunk_count
-            for document_id, chunk_count in fetch_chunk_counts_for_documents(
-                document_ids=updatable_ids,
-                db_session=self.db_session,
-            )
-        }
-
-        doc_id_to_new_chunk_cnt: dict[str, int] = {
-            doc_id: 0 for doc_id in updatable_ids
-        }
-        for chunk in chunks_with_embeddings:
-            if chunk.source_document.id in doc_id_to_new_chunk_cnt:
-                doc_id_to_new_chunk_cnt[chunk.source_document.id] += 1
-
-        # Get ancestor hierarchy node IDs for each document
-        doc_id_to_ancestor_ids = self._get_ancestor_ids_for_documents(
-            context.updatable_docs, tenant_id
-        )
-
-        access_aware_chunks = [
-            DocMetadataAwareIndexChunk.from_index_chunk(
-                index_chunk=chunk,
-                access=doc_id_to_access_info.get(chunk.source_document.id, no_access),
-                document_sets=set(
-                    doc_id_to_document_set.get(chunk.source_document.id, [])
-                ),
-                user_project=[],
-                personas=[],
-                boost=(
-                    context.id_to_boost_map[chunk.source_document.id]
-                    if chunk.source_document.id in context.id_to_boost_map
-                    else DEFAULT_BOOST
-                ),
-                tenant_id=tenant_id,
-                aggregated_chunk_boost_factor=chunk_content_scores[chunk_num],
-                ancestor_hierarchy_node_ids=doc_id_to_ancestor_ids[
-                    chunk.source_document.id
-                ],
-            )
-            for chunk_num, chunk in enumerate(chunks_with_embeddings)
-        ]
-
-        return BuildMetadataAwareChunksResult(
-            chunks=access_aware_chunks,
-            doc_id_to_previous_chunk_cnt=doc_id_to_previous_chunk_cnt,
-            doc_id_to_new_chunk_cnt=doc_id_to_new_chunk_cnt,
-            user_file_id_to_raw_text={},
-            user_file_id_to_token_count={},
+            ),
+            doc_id_to_document_set={
+                document_id: document_sets
+                for document_id, document_sets in fetch_document_sets_for_documents(
+                    document_ids=updatable_ids, db_session=self.db_session
+                )
+            },
+            doc_id_to_ancestor_ids=self._get_ancestor_ids_for_documents(
+                context.updatable_docs, tenant_id
+            ),
+            id_to_boost_map=context.id_to_boost_map,
+            doc_id_to_previous_chunk_cnt={
+                document_id: chunk_count
+                for document_id, chunk_count in fetch_chunk_counts_for_documents(
+                    document_ids=updatable_ids,
+                    db_session=self.db_session,
+                )
+            },
+            doc_id_to_new_chunk_cnt=dict(doc_id_to_new_chunk_cnt),
+            no_access=no_access,
+            tenant_id=tenant_id,
         )
 
     def _get_ancestor_ids_for_documents(
@@ -203,7 +174,7 @@ class DocumentIndexingBatchAdapter:
         context: DocumentBatchPrepareContext,
         updatable_chunk_data: list[UpdatableChunkData],
         filtered_documents: list[Document],
-        result: BuildMetadataAwareChunksResult,
+        enrichment: ChunkEnrichmentContext,
     ) -> None:
         """Finalize DB updates, store plaintext, and mark docs as indexed."""
         updatable_ids = [doc.id for doc in context.updatable_docs]
@@ -227,7 +198,7 @@ class DocumentIndexingBatchAdapter:
 
         update_docs_chunk_count__no_commit(
             document_ids=updatable_ids,
-            doc_id_to_chunk_count=result.doc_id_to_new_chunk_cnt,
+            doc_id_to_chunk_count=enrichment.doc_id_to_new_chunk_cnt,
             db_session=self.db_session,
         )
 
@@ -249,3 +220,52 @@ class DocumentIndexingBatchAdapter:
         )
 
         self.db_session.commit()
+
+
+class DocumentChunkEnricher:
+    """Pre-computed metadata for per-chunk enrichment of connector documents."""
+
+    def __init__(
+        self,
+        doc_id_to_access_info: dict[str, DocumentAccess],
+        doc_id_to_document_set: dict[str, list[str]],
+        doc_id_to_ancestor_ids: dict[str, list[int]],
+        id_to_boost_map: dict[str, int],
+        doc_id_to_previous_chunk_cnt: dict[str, int],
+        doc_id_to_new_chunk_cnt: dict[str, int],
+        no_access: DocumentAccess,
+        tenant_id: str,
+    ) -> None:
+        self._doc_id_to_access_info = doc_id_to_access_info
+        self._doc_id_to_document_set = doc_id_to_document_set
+        self._doc_id_to_ancestor_ids = doc_id_to_ancestor_ids
+        self._id_to_boost_map = id_to_boost_map
+        self._no_access = no_access
+        self._tenant_id = tenant_id
+        self.doc_id_to_previous_chunk_cnt = doc_id_to_previous_chunk_cnt
+        self.doc_id_to_new_chunk_cnt = doc_id_to_new_chunk_cnt
+
+    def enrich_chunk(
+        self, chunk: IndexChunk, score: float
+    ) -> DocMetadataAwareIndexChunk:
+        return DocMetadataAwareIndexChunk.from_index_chunk(
+            index_chunk=chunk,
+            access=self._doc_id_to_access_info.get(
+                chunk.source_document.id, self._no_access
+            ),
+            document_sets=set(
+                self._doc_id_to_document_set.get(chunk.source_document.id, [])
+            ),
+            user_project=[],
+            personas=[],
+            boost=(
+                self._id_to_boost_map[chunk.source_document.id]
+                if chunk.source_document.id in self._id_to_boost_map
+                else DEFAULT_BOOST
+            ),
+            tenant_id=self._tenant_id,
+            aggregated_chunk_boost_factor=score,
+            ancestor_hierarchy_node_ids=self._doc_id_to_ancestor_ids[
+                chunk.source_document.id
+            ],
+        )

backend/onyx/indexing/adapters/user_file_indexing_adapter.py

@@ -1,6 +1,9 @@
+from __future__ import annotations
+
 import contextlib
 import datetime
 import time
+from collections import defaultdict
 from collections.abc import Generator
 from uuid import UUID
 
@@ -24,7 +27,8 @@ from onyx.db.user_file import fetch_persona_ids_for_user_files
 from onyx.db.user_file import fetch_user_project_ids_for_user_files
 from onyx.file_store.utils import store_user_file_plaintext
 from onyx.indexing.indexing_pipeline import DocumentBatchPrepareContext
-from onyx.indexing.models import BuildMetadataAwareChunksResult
+from onyx.indexing.models import ChunkEnrichmentContext
+from onyx.indexing.models import DocAwareChunk
 from onyx.indexing.models import DocMetadataAwareIndexChunk
 from onyx.indexing.models import IndexChunk
 from onyx.indexing.models import UpdatableChunkData
@@ -102,13 +106,20 @@ class UserFileIndexingAdapter:
                 f"Failed to acquire locks after {_NUM_LOCK_ATTEMPTS} attempts for user files: {[doc.id for doc in documents]}"
             )
 
-    def build_metadata_aware_chunks(
+    def prepare_enrichment(
         self,
-        chunks_with_embeddings: list[IndexChunk],
-        chunk_content_scores: list[float],
-        tenant_id: str,
         context: DocumentBatchPrepareContext,
-    ) -> BuildMetadataAwareChunksResult:
+        tenant_id: str,
+        chunks: list[DocAwareChunk],
+    ) -> UserFileChunkEnricher:
+        """Do all DB lookups and pre-compute file metadata from chunks."""
+        updatable_ids = [doc.id for doc in context.updatable_docs]
+
+        doc_id_to_new_chunk_cnt: dict[str, int] = defaultdict(int)
+        content_by_file: dict[str, list[str]] = defaultdict(list)
+        for chunk in chunks:
+            doc_id_to_new_chunk_cnt[chunk.source_document.id] += 1
+            content_by_file[chunk.source_document.id].append(chunk.content)
 
         no_access = DocumentAccess.build(
             user_emails=[],
@@ -118,7 +129,6 @@ class UserFileIndexingAdapter:
             is_public=False,
         )
 
-        updatable_ids = [doc.id for doc in context.updatable_docs]
         user_file_id_to_project_ids = fetch_user_project_ids_for_user_files(
             user_file_ids=updatable_ids,
             db_session=self.db_session,
@@ -139,17 +149,6 @@ class UserFileIndexingAdapter:
             )
         }
 
-        user_file_id_to_new_chunk_cnt: dict[str, int] = {
-            user_file_id: len(
-                [
-                    chunk
-                    for chunk in chunks_with_embeddings
-                    if chunk.source_document.id == user_file_id
-                ]
-            )
-            for user_file_id in updatable_ids
-        }
-
         # Initialize tokenizer used for token count calculation
         try:
             llm = get_default_llm()
@@ -164,15 +163,9 @@ class UserFileIndexingAdapter:
         user_file_id_to_raw_text: dict[str, str] = {}
         user_file_id_to_token_count: dict[str, int | None] = {}
         for user_file_id in updatable_ids:
-            user_file_chunks = [
-                chunk
-                for chunk in chunks_with_embeddings
-                if chunk.source_document.id == user_file_id
-            ]
-            if user_file_chunks:
-                combined_content = " ".join(
-                    [chunk.content for chunk in user_file_chunks]
-                )
+            contents = content_by_file.get(user_file_id)
+            if contents:
+                combined_content = " ".join(contents)
                 user_file_id_to_raw_text[str(user_file_id)] = combined_content
                 token_count: int = (
                     count_tokens(combined_content, llm_tokenizer)
@@ -184,28 +177,16 @@ class UserFileIndexingAdapter:
                 user_file_id_to_raw_text[str(user_file_id)] = ""
                 user_file_id_to_token_count[str(user_file_id)] = None
 
-        access_aware_chunks = [
-            DocMetadataAwareIndexChunk.from_index_chunk(
-                index_chunk=chunk,
-                access=user_file_id_to_access.get(chunk.source_document.id, no_access),
-                document_sets=set(),
-                user_project=user_file_id_to_project_ids.get(
-                    chunk.source_document.id, []
-                ),
-                personas=user_file_id_to_persona_ids.get(chunk.source_document.id, []),
-                boost=DEFAULT_BOOST,
-                tenant_id=tenant_id,
-                aggregated_chunk_boost_factor=chunk_content_scores[chunk_num],
-            )
-            for chunk_num, chunk in enumerate(chunks_with_embeddings)
-        ]
-
-        return BuildMetadataAwareChunksResult(
-            chunks=access_aware_chunks,
+        return UserFileChunkEnricher(
+            user_file_id_to_access=user_file_id_to_access,
+            user_file_id_to_project_ids=user_file_id_to_project_ids,
+            user_file_id_to_persona_ids=user_file_id_to_persona_ids,
             doc_id_to_previous_chunk_cnt=user_file_id_to_previous_chunk_cnt,
-            doc_id_to_new_chunk_cnt=user_file_id_to_new_chunk_cnt,
+            doc_id_to_new_chunk_cnt=dict(doc_id_to_new_chunk_cnt),
             user_file_id_to_raw_text=user_file_id_to_raw_text,
             user_file_id_to_token_count=user_file_id_to_token_count,
+            no_access=no_access,
+            tenant_id=tenant_id,
         )
 
     def _notify_assistant_owners_if_files_ready(
@@ -249,8 +230,9 @@ class UserFileIndexingAdapter:
         context: DocumentBatchPrepareContext,
         updatable_chunk_data: list[UpdatableChunkData],  # noqa: ARG002
         filtered_documents: list[Document],  # noqa: ARG002
-        result: BuildMetadataAwareChunksResult,
+        enrichment: ChunkEnrichmentContext,
     ) -> None:
+        assert isinstance(enrichment, UserFileChunkEnricher)
         user_file_ids = [doc.id for doc in context.updatable_docs]
 
         user_files = (
@@ -266,8 +248,10 @@ class UserFileIndexingAdapter:
             user_file.last_project_sync_at = datetime.datetime.now(
                 datetime.timezone.utc
             )
-            user_file.chunk_count = result.doc_id_to_new_chunk_cnt[str(user_file.id)]
-            user_file.token_count = result.user_file_id_to_token_count[
+            user_file.chunk_count = enrichment.doc_id_to_new_chunk_cnt.get(
+                str(user_file.id), 0
+            )
+            user_file.token_count = enrichment.user_file_id_to_token_count[
                 str(user_file.id)
             ]
 
@@ -279,8 +263,54 @@ class UserFileIndexingAdapter:
         # Store the plaintext in the file store for faster retrieval
         # NOTE: this creates its own session to avoid committing the overall
         # transaction.
-        for user_file_id, raw_text in result.user_file_id_to_raw_text.items():
+        for user_file_id, raw_text in enrichment.user_file_id_to_raw_text.items():
             store_user_file_plaintext(
                 user_file_id=UUID(user_file_id),
                 plaintext_content=raw_text,
             )
+
+
+class UserFileChunkEnricher:
+    """Pre-computed metadata for per-chunk enrichment of user-uploaded files."""
+
+    def __init__(
+        self,
+        user_file_id_to_access: dict[str, DocumentAccess],
+        user_file_id_to_project_ids: dict[str, list[int]],
+        user_file_id_to_persona_ids: dict[str, list[int]],
+        doc_id_to_previous_chunk_cnt: dict[str, int],
+        doc_id_to_new_chunk_cnt: dict[str, int],
+        user_file_id_to_raw_text: dict[str, str],
+        user_file_id_to_token_count: dict[str, int | None],
+        no_access: DocumentAccess,
+        tenant_id: str,
+    ) -> None:
+        self._user_file_id_to_access = user_file_id_to_access
+        self._user_file_id_to_project_ids = user_file_id_to_project_ids
+        self._user_file_id_to_persona_ids = user_file_id_to_persona_ids
+        self._no_access = no_access
+        self._tenant_id = tenant_id
+        self.doc_id_to_previous_chunk_cnt = doc_id_to_previous_chunk_cnt
+        self.doc_id_to_new_chunk_cnt = doc_id_to_new_chunk_cnt
+        self.user_file_id_to_raw_text = user_file_id_to_raw_text
+        self.user_file_id_to_token_count = user_file_id_to_token_count
+
+    def enrich_chunk(
+        self, chunk: IndexChunk, score: float
+    ) -> DocMetadataAwareIndexChunk:
+        return DocMetadataAwareIndexChunk.from_index_chunk(
+            index_chunk=chunk,
+            access=self._user_file_id_to_access.get(
+                chunk.source_document.id, self._no_access
+            ),
+            document_sets=set(),
+            user_project=self._user_file_id_to_project_ids.get(
+                chunk.source_document.id, []
+            ),
+            personas=self._user_file_id_to_persona_ids.get(
+                chunk.source_document.id, []
+            ),
+            boost=DEFAULT_BOOST,
+            tenant_id=self._tenant_id,
+            aggregated_chunk_boost_factor=score,
+        )

backend/onyx/indexing/chunk_batch_store.py

@@ -0,0 +1,89 @@
+import pickle
+import shutil
+import tempfile
+from collections.abc import Iterator
+from pathlib import Path
+
+from onyx.indexing.models import IndexChunk
+
+
+class ChunkBatchStore:
+    """Manages serialization of embedded chunks to a temporary directory.
+
+    Owns the temp directory lifetime and provides save/load/stream/scrub
+    operations.
+
+    Use as a context manager to ensure cleanup::
+
+        with ChunkBatchStore() as store:
+            store.save(chunks, batch_idx=0)
+            for chunk in store.stream():
+                ...
+    """
+
+    _EXT = ".pkl"
+
+    def __init__(self) -> None:
+        self._tmpdir: Path | None = None
+
+    # -- context manager -----------------------------------------------------
+
+    def __enter__(self) -> "ChunkBatchStore":
+        self._tmpdir = Path(tempfile.mkdtemp(prefix="onyx_embeddings_"))
+        return self
+
+    def __exit__(self, *_exc: object) -> None:
+        if self._tmpdir is not None:
+            shutil.rmtree(self._tmpdir, ignore_errors=True)
+            self._tmpdir = None
+
+    @property
+    def _dir(self) -> Path:
+        assert self._tmpdir is not None, "ChunkBatchStore used outside context manager"
+        return self._tmpdir
+
+    # -- storage primitives --------------------------------------------------
+
+    def save(self, chunks: list[IndexChunk], batch_idx: int) -> None:
+        """Serialize a batch of embedded chunks to disk."""
+        with open(self._dir / f"batch_{batch_idx}{self._EXT}", "wb") as f:
+            pickle.dump(chunks, f)
+
+    def _load(self, batch_file: Path) -> list[IndexChunk]:
+        """Deserialize a batch of embedded chunks from a file."""
+        with open(batch_file, "rb") as f:
+            return pickle.load(f)
+
+    def _batch_files(self) -> list[Path]:
+        """Return batch files sorted by numeric index."""
+        return sorted(
+            self._dir.glob(f"batch_*{self._EXT}"),
+            key=lambda p: int(p.stem.removeprefix("batch_")),
+        )
+
+    # -- higher-level operations ---------------------------------------------
+
+    def stream(self) -> Iterator[IndexChunk]:
+        """Yield all chunks across all batch files.
+
+        Each call returns a fresh generator, so the data can be iterated
+        multiple times (e.g. once per document index).
+        """
+        for batch_file in self._batch_files():
+            yield from self._load(batch_file)
+
+    def scrub_failed_docs(self, failed_doc_ids: set[str]) -> None:
+        """Remove chunks belonging to *failed_doc_ids* from all batch files.
+
+        When a document fails embedding in batch N, earlier batches may
+        already contain successfully embedded chunks for that document.
+        This ensures the output is all-or-nothing per document.
+        """
+        for batch_file in self._batch_files():
+            batch_chunks = self._load(batch_file)
+            cleaned = [
+                c for c in batch_chunks if c.source_document.id not in failed_doc_ids
+            ]
+            if len(cleaned) != len(batch_chunks):
+                with open(batch_file, "wb") as f:
+                    pickle.dump(cleaned, f)

backend/onyx/indexing/indexing_pipeline.py

@@ -1,5 +1,8 @@
 from collections import defaultdict
 from collections.abc import Callable
+from collections.abc import Generator
+from collections.abc import Iterator
+from contextlib import contextmanager
 from typing import Protocol
 
 from pydantic import BaseModel
@@ -9,6 +12,7 @@ from sqlalchemy.orm import Session
 from onyx.configs.app_configs import DEFAULT_CONTEXTUAL_RAG_LLM_NAME
 from onyx.configs.app_configs import DEFAULT_CONTEXTUAL_RAG_LLM_PROVIDER
 from onyx.configs.app_configs import ENABLE_CONTEXTUAL_RAG
+from onyx.configs.app_configs import MAX_CHUNKS_PER_DOC_BATCH
 from onyx.configs.app_configs import MAX_DOCUMENT_CHARS
 from onyx.configs.app_configs import MAX_TOKENS_FOR_FULL_INCLUSION
 from onyx.configs.app_configs import USE_CHUNK_SUMMARY
@@ -43,10 +47,12 @@ from onyx.document_index.interfaces import DocumentMetadata
 from onyx.document_index.interfaces import IndexBatchParams
 from onyx.file_processing.image_summarization import summarize_image_with_error_handling
 from onyx.file_store.file_store import get_default_file_store
+from onyx.indexing.chunk_batch_store import ChunkBatchStore
 from onyx.indexing.chunker import Chunker
 from onyx.indexing.embedder import embed_chunks_with_failure_handling
 from onyx.indexing.embedder import IndexingEmbedder
 from onyx.indexing.models import DocAwareChunk
+from onyx.indexing.models import DocMetadataAwareIndexChunk
 from onyx.indexing.models import IndexingBatchAdapter
 from onyx.indexing.models import UpdatableChunkData
 from onyx.indexing.vector_db_insertion import write_chunks_to_vector_db_with_backoff
@@ -63,6 +69,7 @@ from onyx.natural_language_processing.utils import tokenizer_trim_middle
 from onyx.prompts.contextual_retrieval import CONTEXTUAL_RAG_PROMPT1
 from onyx.prompts.contextual_retrieval import CONTEXTUAL_RAG_PROMPT2
 from onyx.prompts.contextual_retrieval import DOCUMENT_SUMMARY_PROMPT
+from onyx.utils.batching import batch_generator
 from onyx.utils.logger import setup_logger
 from onyx.utils.postgres_sanitization import sanitize_documents_for_postgres
 from onyx.utils.threadpool_concurrency import run_functions_tuples_in_parallel
@@ -91,6 +98,20 @@ class IndexingPipelineResult(BaseModel):
 
     failures: list[ConnectorFailure]
 
+    @classmethod
+    def empty(cls, total_docs: int) -> "IndexingPipelineResult":
+        return cls(
+            new_docs=0,
+            total_docs=total_docs,
+            total_chunks=0,
+            failures=[],
+        )
+
+
+class ChunkEmbeddingResult(BaseModel):
+    successful_chunk_ids: list[tuple[int, str]]  # (chunk_id, document_id)
+    connector_failures: list[ConnectorFailure]
+
 
 class IndexingPipelineProtocol(Protocol):
     def __call__(
@@ -139,6 +160,110 @@ def _upsert_documents_in_db(
         )
 
 
+def _get_failed_doc_ids(failures: list[ConnectorFailure]) -> set[str]:
+    """Extract document IDs from a list of connector failures."""
+    return {f.failed_document.document_id for f in failures if f.failed_document}
+
+
+def _embed_chunks_to_store(
+    chunks: list[DocAwareChunk],
+    embedder: IndexingEmbedder,
+    tenant_id: str,
+    request_id: str | None,
+    store: ChunkBatchStore,
+) -> ChunkEmbeddingResult:
+    """Embed chunks in batches, spilling each batch to *store*.
+
+    If a document fails embedding in any batch, its chunks are excluded from
+    all batches (including earlier ones already written) so that the output
+    is all-or-nothing per document.
+    """
+    successful_chunk_ids: list[tuple[int, str]] = []
+    all_embedding_failures: list[ConnectorFailure] = []
+    # Track failed doc IDs across all batches so that a failure in batch N
+    # causes chunks for that doc to be skipped in batch N+1 and stripped
+    # from earlier batches.
+    all_failed_doc_ids: set[str] = set()
+
+    for batch_idx, chunk_batch in enumerate(
+        batch_generator(chunks, MAX_CHUNKS_PER_DOC_BATCH)
+    ):
+        # Skip chunks belonging to documents that failed in earlier batches.
+        chunk_batch = [
+            c for c in chunk_batch if c.source_document.id not in all_failed_doc_ids
+        ]
+        if not chunk_batch:
+            continue
+
+        logger.debug(f"Embedding batch {batch_idx}: {len(chunk_batch)} chunks")
+
+        chunks_with_embeddings, embedding_failures = embed_chunks_with_failure_handling(
+            chunks=chunk_batch,
+            embedder=embedder,
+            tenant_id=tenant_id,
+            request_id=request_id,
+        )
+        all_embedding_failures.extend(embedding_failures)
+        all_failed_doc_ids.update(_get_failed_doc_ids(embedding_failures))
+
+        # Only keep successfully embedded chunks for non-failed docs.
+        chunks_with_embeddings = [
+            c
+            for c in chunks_with_embeddings
+            if c.source_document.id not in all_failed_doc_ids
+        ]
+
+        successful_chunk_ids.extend(
+            (c.chunk_id, c.source_document.id) for c in chunks_with_embeddings
+        )
+
+        store.save(chunks_with_embeddings, batch_idx)
+        del chunks_with_embeddings
+
+    # Scrub earlier batches for docs that failed in later batches.
+    if all_failed_doc_ids:
+        store.scrub_failed_docs(all_failed_doc_ids)
+        successful_chunk_ids = [
+            (chunk_id, doc_id)
+            for chunk_id, doc_id in successful_chunk_ids
+            if doc_id not in all_failed_doc_ids
+        ]
+
+    return ChunkEmbeddingResult(
+        successful_chunk_ids=successful_chunk_ids,
+        connector_failures=all_embedding_failures,
+    )
+
+
+@contextmanager
+def embed_and_stream(
+    chunks: list[DocAwareChunk],
+    embedder: IndexingEmbedder,
+    tenant_id: str,
+    request_id: str | None,
+) -> Generator[tuple[ChunkEmbeddingResult, ChunkBatchStore], None, None]:
+    """Embed chunks to disk and yield a ``(result, store)`` pair.
+
+    The store owns the temp directory — files are cleaned up when the context
+    manager exits.
+
+    Usage::
+
+        with embed_and_stream(chunks, embedder, tenant_id, req_id) as (result, store):
+            for chunk in store.stream():
+                ...
+    """
+    with ChunkBatchStore() as store:
+        result = _embed_chunks_to_store(
+            chunks=chunks,
+            embedder=embedder,
+            tenant_id=tenant_id,
+            request_id=request_id,
+            store=store,
+        )
+        yield result, store
+
+
 def get_doc_ids_to_update(
     documents: list[Document], db_docs: list[DBDocument]
 ) -> list[Document]:
@@ -637,6 +762,29 @@ def add_contextual_summaries(
     return chunks
 
 
+def _verify_indexing_completeness(
+    insertion_records: list[DocumentInsertionRecord],
+    write_failures: list[ConnectorFailure],
+    embedding_failed_doc_ids: set[str],
+    updatable_ids: list[str],
+    document_index_name: str,
+) -> None:
+    """Verify that every updatable document was either indexed or reported as failed."""
+    all_returned_doc_ids = (
+        {r.document_id for r in insertion_records}
+        | {f.failed_document.document_id for f in write_failures if f.failed_document}
+        | embedding_failed_doc_ids
+    )
+    if all_returned_doc_ids != set(updatable_ids):
+        raise RuntimeError(
+            f"Some documents were not successfully indexed. "
+            f"Updatable IDs: {updatable_ids}, "
+            f"Returned IDs: {all_returned_doc_ids}. "
+            f"This should never happen. "
+            f"This occured for document index {document_index_name}"
+        )
+
+
 @log_function_time(debug_only=True)
 def index_doc_batch(
     *,
@@ -672,12 +820,7 @@ def index_doc_batch(
     filtered_documents = filter_fnc(document_batch)
     context = adapter.prepare(filtered_documents, ignore_time_skip)
     if not context:
-        return IndexingPipelineResult(
-            new_docs=0,
-            total_docs=len(filtered_documents),
-            total_chunks=0,
-            failures=[],
-        )
+        return IndexingPipelineResult.empty(len(filtered_documents))
 
     # Convert documents to IndexingDocument objects with processed section
     # logger.debug("Processing image sections")
@@ -716,117 +859,99 @@ def index_doc_batch(
         )
 
     logger.debug("Starting embedding")
-    chunks_with_embeddings, embedding_failures = (
-        embed_chunks_with_failure_handling(
-            chunks=chunks,
-            embedder=embedder,
-            tenant_id=tenant_id,
-            request_id=request_id,
-        )
-        if chunks
-        else ([], [])
-    )
+    with embed_and_stream(chunks, embedder, tenant_id, request_id) as (
+        embedding_result,
+        chunk_store,
+    ):
+        updatable_ids = [doc.id for doc in context.updatable_docs]
+        updatable_chunk_data = [
+            UpdatableChunkData(
+                chunk_id=chunk_id,
+                document_id=document_id,
+                boost_score=1.0,
+            )
+            for chunk_id, document_id in embedding_result.successful_chunk_ids
+        ]
 
-    chunk_content_scores = [1.0] * len(chunks_with_embeddings)
-
-    updatable_ids = [doc.id for doc in context.updatable_docs]
-    updatable_chunk_data = [
-        UpdatableChunkData(
-            chunk_id=chunk.chunk_id,
-            document_id=chunk.source_document.id,
-            boost_score=score,
-        )
-        for chunk, score in zip(chunks_with_embeddings, chunk_content_scores)
-    ]
-
-    # Acquires a lock on the documents so that no other process can modify them
-    # NOTE: don't need to acquire till here, since this is when the actual race condition
-    # with Vespa can occur.
-    with adapter.lock_context(context.updatable_docs):
-        # we're concerned about race conditions where multiple simultaneous indexings might result
-        # in one set of metadata overwriting another one in vespa.
-        # we still write data here for the immediate and most likely correct sync, but
-        # to resolve this, an update of the last modified field at the end of this loop
-        # always triggers a final metadata sync via the celery queue
-        result = adapter.build_metadata_aware_chunks(
-            chunks_with_embeddings=chunks_with_embeddings,
-            chunk_content_scores=chunk_content_scores,
-            tenant_id=tenant_id,
-            context=context,
+        embedding_failed_doc_ids = _get_failed_doc_ids(
+            embedding_result.connector_failures
         )
 
-        short_descriptor_list = [chunk.to_short_descriptor() for chunk in result.chunks]
-        short_descriptor_log = str(short_descriptor_list)[:1024]
-        logger.debug(f"Indexing the following chunks: {short_descriptor_log}")
+        # Filter to only successfully embedded chunks so
+        # doc_id_to_new_chunk_cnt reflects what's actually written to Vespa.
+        embedded_chunks = [
+            c for c in chunks if c.source_document.id not in embedding_failed_doc_ids
+        ]
 
-        primary_doc_idx_insertion_records: list[DocumentInsertionRecord] | None = None
-        primary_doc_idx_vector_db_write_failures: list[ConnectorFailure] | None = None
-        for document_index in document_indices:
-            # A document will not be spread across different batches, so all the
-            # documents with chunks in this set, are fully represented by the chunks
-            # in this set
-            (
-                insertion_records,
-                vector_db_write_failures,
-            ) = write_chunks_to_vector_db_with_backoff(
-                document_index=document_index,
-                chunks=result.chunks,
-                index_batch_params=IndexBatchParams(
-                    doc_id_to_previous_chunk_cnt=result.doc_id_to_previous_chunk_cnt,
-                    doc_id_to_new_chunk_cnt=result.doc_id_to_new_chunk_cnt,
-                    tenant_id=tenant_id,
-                    large_chunks_enabled=chunker.enable_large_chunks,
-                ),
+        # Acquires a lock on the documents so that no other process can modify
+        # them.  Not needed until here, since this is when the actual race
+        # condition with vector db can occur.
+        with adapter.lock_context(context.updatable_docs):
+            enricher = adapter.prepare_enrichment(
+                context=context,
+                tenant_id=tenant_id,
+                chunks=embedded_chunks,
             )
 
-            all_returned_doc_ids: set[str] = (
-                {record.document_id for record in insertion_records}
-                .union(
-                    {
-                        record.failed_document.document_id
-                        for record in vector_db_write_failures
-                        if record.failed_document
-                    }
-                )
-                .union(
-                    {
-                        record.failed_document.document_id
-                        for record in embedding_failures
-                        if record.failed_document
-                    }
-                )
+            index_batch_params = IndexBatchParams(
+                doc_id_to_previous_chunk_cnt=enricher.doc_id_to_previous_chunk_cnt,
+                doc_id_to_new_chunk_cnt=enricher.doc_id_to_new_chunk_cnt,
+                tenant_id=tenant_id,
+                large_chunks_enabled=chunker.enable_large_chunks,
             )
-            if all_returned_doc_ids != set(updatable_ids):
-                raise RuntimeError(
-                    f"Some documents were not successfully indexed. "
-                    f"Updatable IDs: {updatable_ids}, "
-                    f"Returned IDs: {all_returned_doc_ids}. "
-                    "This should never happen."
-                    f"This occured for document index {document_index.__class__.__name__}"
-                )
-            # We treat the first document index we got as the primary one used
-            # for reporting the state of indexing.
-            if primary_doc_idx_insertion_records is None:
-                primary_doc_idx_insertion_records = insertion_records
-            if primary_doc_idx_vector_db_write_failures is None:
-                primary_doc_idx_vector_db_write_failures = vector_db_write_failures
 
-        adapter.post_index(
-            context=context,
-            updatable_chunk_data=updatable_chunk_data,
-            filtered_documents=filtered_documents,
-            result=result,
-        )
+            primary_doc_idx_insertion_records: list[DocumentInsertionRecord] | None = (
+                None
+            )
+            primary_doc_idx_vector_db_write_failures: list[ConnectorFailure] | None = (
+                None
+            )
+
+            for document_index in document_indices:
+
+                def _enriched_stream() -> Iterator[DocMetadataAwareIndexChunk]:
+                    for chunk in chunk_store.stream():
+                        yield enricher.enrich_chunk(chunk, 1.0)
+
+                insertion_records, write_failures = (
+                    write_chunks_to_vector_db_with_backoff(
+                        document_index=document_index,
+                        make_chunks=_enriched_stream,
+                        index_batch_params=index_batch_params,
+                    )
+                )
+
+                _verify_indexing_completeness(
+                    insertion_records=insertion_records,
+                    write_failures=write_failures,
+                    embedding_failed_doc_ids=embedding_failed_doc_ids,
+                    updatable_ids=updatable_ids,
+                    document_index_name=document_index.__class__.__name__,
+                )
+                # We treat the first document index we got as the primary one used
+                # for reporting the state of indexing.
+                if primary_doc_idx_insertion_records is None:
+                    primary_doc_idx_insertion_records = insertion_records
+                if primary_doc_idx_vector_db_write_failures is None:
+                    primary_doc_idx_vector_db_write_failures = write_failures
+
+            adapter.post_index(
+                context=context,
+                updatable_chunk_data=updatable_chunk_data,
+                filtered_documents=filtered_documents,
+                enrichment=enricher,
+            )
 
     assert primary_doc_idx_insertion_records is not None
     assert primary_doc_idx_vector_db_write_failures is not None
     return IndexingPipelineResult(
-        new_docs=len(
-            [r for r in primary_doc_idx_insertion_records if not r.already_existed]
+        new_docs=sum(
+            1 for r in primary_doc_idx_insertion_records if not r.already_existed
         ),
         total_docs=len(filtered_documents),
-        total_chunks=len(chunks_with_embeddings),
-        failures=primary_doc_idx_vector_db_write_failures + embedding_failures,
+        total_chunks=len(embedding_result.successful_chunk_ids),
+        failures=primary_doc_idx_vector_db_write_failures
+        + embedding_result.connector_failures,
     )
 
 

backend/onyx/indexing/models.py

@@ -235,12 +235,16 @@ class UpdatableChunkData(BaseModel):
     boost_score: float
 
 
-class BuildMetadataAwareChunksResult(BaseModel):
-    chunks: list[DocMetadataAwareIndexChunk]
+class ChunkEnrichmentContext(Protocol):
+    """Returned by prepare_enrichment. Holds pre-computed metadata lookups
+    and provides per-chunk enrichment."""
+
     doc_id_to_previous_chunk_cnt: dict[str, int]
     doc_id_to_new_chunk_cnt: dict[str, int]
-    user_file_id_to_raw_text: dict[str, str]
-    user_file_id_to_token_count: dict[str, int | None]
+
+    def enrich_chunk(
+        self, chunk: IndexChunk, score: float
+    ) -> DocMetadataAwareIndexChunk: ...
 
 
 class IndexingBatchAdapter(Protocol):
@@ -254,18 +258,24 @@ class IndexingBatchAdapter(Protocol):
     ) -> Generator[TransactionalContext, None, None]:
         """Provide a transaction/row-lock context for critical updates."""
 
-    def build_metadata_aware_chunks(
+    def prepare_enrichment(
         self,
-        chunks_with_embeddings: list[IndexChunk],
-        chunk_content_scores: list[float],
-        tenant_id: str,
         context: "DocumentBatchPrepareContext",
-    ) -> BuildMetadataAwareChunksResult: ...
+        tenant_id: str,
+        chunks: list[DocAwareChunk],
+    ) -> ChunkEnrichmentContext:
+        """Prepare per-chunk enrichment data (access, document sets, boost, etc.).
+
+        Precondition: ``chunks`` have already been through the embedding step
+        (i.e. they are ``IndexChunk`` instances with populated embeddings,
+        passed here as the base ``DocAwareChunk`` type).
+        """
+        ...
 
     def post_index(
         self,
         context: "DocumentBatchPrepareContext",
         updatable_chunk_data: list[UpdatableChunkData],
         filtered_documents: list[Document],
-        result: BuildMetadataAwareChunksResult,
+        enrichment: ChunkEnrichmentContext,
     ) -> None: ...

backend/onyx/indexing/vector_db_insertion.py

@@ -1,6 +1,9 @@
 import time
-from collections import defaultdict
+from collections.abc import Callable
+from collections.abc import Iterable
 from http import HTTPStatus
+from itertools import chain
+from itertools import groupby
 
 import httpx
 
@@ -28,22 +31,22 @@ def _log_insufficient_storage_error(e: Exception) -> None:
 
 def write_chunks_to_vector_db_with_backoff(
     document_index: DocumentIndex,
-    chunks: list[DocMetadataAwareIndexChunk],
+    make_chunks: Callable[[], Iterable[DocMetadataAwareIndexChunk]],
     index_batch_params: IndexBatchParams,
 ) -> tuple[list[DocumentInsertionRecord], list[ConnectorFailure]]:
     """Tries to insert all chunks in one large batch. If that batch fails for any reason,
     goes document by document to isolate the failure(s).
 
     IMPORTANT: must pass in whole documents at a time not individual chunks, since the
-    vector DB interface assumes that all chunks for a single document are present.
+    vector DB interface assumes that all chunks for a single document are present. The
+    chunks must also be in contiguous batches
     """
-
     # first try to write the chunks to the vector db
     try:
         return (
             list(
                 document_index.index(
-                    chunks=chunks,
+                    chunks=make_chunks(),
                     index_batch_params=index_batch_params,
                 )
             ),
@@ -60,14 +63,23 @@ def write_chunks_to_vector_db_with_backoff(
         # wait a couple seconds just to give the vector db a chance to recover
         time.sleep(2)
 
-    # try writing each doc one by one
-    chunks_for_docs: dict[str, list[DocMetadataAwareIndexChunk]] = defaultdict(list)
-    for chunk in chunks:
-        chunks_for_docs[chunk.source_document.id].append(chunk)
-
     insertion_records: list[DocumentInsertionRecord] = []
     failures: list[ConnectorFailure] = []
-    for doc_id, chunks_for_doc in chunks_for_docs.items():
+
+    def key(chunk: DocMetadataAwareIndexChunk) -> str:
+        return chunk.source_document.id
+
+    seen_doc_ids: set[str] = set()
+    for doc_id, chunks_for_doc in groupby(make_chunks(), key=key):
+        if doc_id in seen_doc_ids:
+            raise RuntimeError(
+                f"Doc chunks are not arriving in order. Current doc_id={doc_id}, seen_doc_ids={list(seen_doc_ids)}"
+            )
+        seen_doc_ids.add(doc_id)
+
+        first_chunk = next(chunks_for_doc)
+        chunks_for_doc = chain([first_chunk], chunks_for_doc)
+
         try:
             insertion_records.extend(
                 document_index.index(
@@ -87,9 +99,7 @@ def write_chunks_to_vector_db_with_backoff(
                 ConnectorFailure(
                     failed_document=DocumentFailure(
                         document_id=doc_id,
-                        document_link=(
-                            chunks_for_doc[0].get_link() if chunks_for_doc else None
-                        ),
+                        document_link=first_chunk.get_link(),
                     ),
                     failure_message=str(e),
                     exception=e,

backend/onyx/llm/multi_llm.py

@@ -185,6 +185,21 @@ def _messages_contain_tool_content(messages: list[dict[str, Any]]) -> bool:
     return False
 
 
+def _prompt_contains_tool_call_history(prompt: LanguageModelInput) -> bool:
+    """Check if the prompt contains any assistant messages with tool_calls.
+
+    When Anthropic's extended thinking is enabled, the API requires every
+    assistant message to start with a thinking block before any tool_use
+    blocks.  Since we don't preserve thinking_blocks (they carry
+    cryptographic signatures that can't be reconstructed), we must skip
+    the thinking param whenever history contains prior tool-calling turns.
+    """
+    from onyx.llm.models import AssistantMessage
+
+    msgs = prompt if isinstance(prompt, list) else [prompt]
+    return any(isinstance(msg, AssistantMessage) and msg.tool_calls for msg in msgs)
+
+
 def _is_vertex_model_rejecting_output_config(model_name: str) -> bool:
     normalized_model_name = model_name.lower()
     return any(
@@ -466,7 +481,20 @@ class LitellmLLM(LLM):
                     reasoning_effort
                 )
 
-                if budget_tokens is not None:
+                # Anthropic requires every assistant message with tool_use
+                # blocks to start with a thinking block that carries a
+                # cryptographic signature.  We don't preserve those blocks
+                # across turns, so skip thinking when the history already
+                # contains tool-calling assistant messages.  LiteLLM's
+                # modify_params workaround doesn't cover all providers
+                # (notably Bedrock).
+                can_enable_thinking = (
+                    budget_tokens is not None
+                    and not _prompt_contains_tool_call_history(prompt)
+                )
+
+                if can_enable_thinking:
+                    assert budget_tokens is not None  # mypy
                     if max_tokens is not None:
                         # Anthropic has a weird rule where max token has to be at least as much as budget tokens if set
                         # and the minimum budget tokens is 1024

backend/onyx/main.py

@@ -439,6 +439,7 @@ def get_application(lifespan_override: Lifespan | None = None) -> FastAPI:
             dsn=SENTRY_DSN,
             integrations=[StarletteIntegration(), FastApiIntegration()],
             traces_sample_rate=0.1,
+            release=__version__,
         )
         logger.info("Sentry initialized")
     else:

backend/requirements/default.txt

@@ -187,7 +187,7 @@ coloredlogs==15.0.1
     # via onnxruntime
 courlan==1.3.2
     # via trafilatura
-cryptography==46.0.5
+cryptography==46.0.6
     # via
     #   authlib
     #   google-auth
@@ -449,7 +449,7 @@ kombu==5.5.4
     # via celery
 kubernetes==31.0.0
     # via onyx
-langchain-core==1.2.11
+langchain-core==1.2.22
     # via onyx
 langdetect==1.0.9
     # via unstructured
@@ -735,7 +735,7 @@ pyee==13.0.0
     # via playwright
 pygithub==2.5.0
     # via onyx
-pygments==2.19.2
+pygments==2.20.0
     # via rich
 pyjwt==2.12.0
     # via

backend/requirements/dev.txt

@@ -97,7 +97,7 @@ comm==0.2.3
     # via ipykernel
 contourpy==1.3.3
     # via matplotlib
-cryptography==46.0.5
+cryptography==46.0.6
     # via
     #   google-auth
     #   pyjwt
@@ -349,7 +349,7 @@ pydantic-core==2.33.2
     # via pydantic
 pydantic-settings==2.12.0
     # via mcp
-pygments==2.19.2
+pygments==2.20.0
     # via
     #   ipython
     #   ipython-pygments-lexers

backend/requirements/ee.txt

@@ -76,7 +76,7 @@ colorama==0.4.6 ; sys_platform == 'win32'
     # via
     #   click
     #   tqdm
-cryptography==46.0.5
+cryptography==46.0.6
     # via
     #   google-auth
     #   pyjwt

backend/requirements/model_server.txt

@@ -92,7 +92,7 @@ colorama==0.4.6 ; sys_platform == 'win32'
     # via
     #   click
     #   tqdm
-cryptography==46.0.5
+cryptography==46.0.6
     # via
     #   google-auth
     #   pyjwt

backend/tests/external_dependency_unit/celery/test_user_file_indexing_adapter.py

@@ -1,7 +1,7 @@
 """
 External dependency unit tests for UserFileIndexingAdapter metadata writing.
 
-Validates that build_metadata_aware_chunks produces DocMetadataAwareIndexChunk
+Validates that prepare_enrichment produces DocMetadataAwareIndexChunk
 objects with both `user_project` and `personas` fields populated correctly
 based on actual DB associations.
 
@@ -127,7 +127,7 @@ def _make_index_chunk(user_file: UserFile) -> IndexChunk:
 
 
 class TestAdapterWritesBothMetadataFields:
-    """build_metadata_aware_chunks must populate user_project AND personas."""
+    """prepare_enrichment must populate user_project AND personas."""
 
     @patch(
         "onyx.indexing.adapters.user_file_indexing_adapter.get_default_llm",
@@ -153,15 +153,13 @@ class TestAdapterWritesBothMetadataFields:
         doc = chunk.source_document
         context = DocumentBatchPrepareContext(updatable_docs=[doc], id_to_boost_map={})
 
-        result = adapter.build_metadata_aware_chunks(
-            chunks_with_embeddings=[chunk],
-            chunk_content_scores=[1.0],
-            tenant_id=TEST_TENANT_ID,
+        enricher = adapter.prepare_enrichment(
             context=context,
+            tenant_id=TEST_TENANT_ID,
+            chunks=[chunk],
         )
+        aware_chunk = enricher.enrich_chunk(chunk, 1.0)
 
-        assert len(result.chunks) == 1
-        aware_chunk = result.chunks[0]
         assert persona.id in aware_chunk.personas
         assert aware_chunk.user_project == []
 
@@ -190,15 +188,13 @@ class TestAdapterWritesBothMetadataFields:
             updatable_docs=[chunk.source_document], id_to_boost_map={}
         )
 
-        result = adapter.build_metadata_aware_chunks(
-            chunks_with_embeddings=[chunk],
-            chunk_content_scores=[1.0],
-            tenant_id=TEST_TENANT_ID,
+        enricher = adapter.prepare_enrichment(
             context=context,
+            tenant_id=TEST_TENANT_ID,
+            chunks=[chunk],
         )
+        aware_chunk = enricher.enrich_chunk(chunk, 1.0)
 
-        assert len(result.chunks) == 1
-        aware_chunk = result.chunks[0]
         assert project.id in aware_chunk.user_project
         assert aware_chunk.personas == []
 
@@ -229,14 +225,13 @@ class TestAdapterWritesBothMetadataFields:
             updatable_docs=[chunk.source_document], id_to_boost_map={}
         )
 
-        result = adapter.build_metadata_aware_chunks(
-            chunks_with_embeddings=[chunk],
-            chunk_content_scores=[1.0],
-            tenant_id=TEST_TENANT_ID,
+        enricher = adapter.prepare_enrichment(
             context=context,
+            tenant_id=TEST_TENANT_ID,
+            chunks=[chunk],
         )
+        aware_chunk = enricher.enrich_chunk(chunk, 1.0)
 
-        aware_chunk = result.chunks[0]
         assert persona.id in aware_chunk.personas
         assert project.id in aware_chunk.user_project
 
@@ -261,14 +256,13 @@ class TestAdapterWritesBothMetadataFields:
             updatable_docs=[chunk.source_document], id_to_boost_map={}
         )
 
-        result = adapter.build_metadata_aware_chunks(
-            chunks_with_embeddings=[chunk],
-            chunk_content_scores=[1.0],
-            tenant_id=TEST_TENANT_ID,
+        enricher = adapter.prepare_enrichment(
             context=context,
+            tenant_id=TEST_TENANT_ID,
+            chunks=[chunk],
         )
+        aware_chunk = enricher.enrich_chunk(chunk, 1.0)
 
-        aware_chunk = result.chunks[0]
         assert aware_chunk.personas == []
         assert aware_chunk.user_project == []
 
@@ -300,12 +294,11 @@ class TestAdapterWritesBothMetadataFields:
             updatable_docs=[chunk.source_document], id_to_boost_map={}
         )
 
-        result = adapter.build_metadata_aware_chunks(
-            chunks_with_embeddings=[chunk],
-            chunk_content_scores=[1.0],
-            tenant_id=TEST_TENANT_ID,
+        enricher = adapter.prepare_enrichment(
             context=context,
+            tenant_id=TEST_TENANT_ID,
+            chunks=[chunk],
         )
+        aware_chunk = enricher.enrich_chunk(chunk, 1.0)
 
-        aware_chunk = result.chunks[0]
         assert set(aware_chunk.personas) == {persona_a.id, persona_b.id}

backend/tests/unit/ee/onyx/background/celery/tasks/ttl_management/test_ttl_task.py

@@ -0,0 +1,109 @@
+"""Tests for TTL management task resilience."""
+
+from typing import Any
+from unittest.mock import MagicMock
+from unittest.mock import patch
+from uuid import uuid4
+
+
+_TASK_MODULE = "ee.onyx.background.celery.tasks.ttl_management.tasks"
+
+
+def _setup_db_session_mock(mock_get_db_session: MagicMock) -> None:
+    mock_db_session = MagicMock()
+    mock_get_db_session.return_value.__enter__ = MagicMock(
+        return_value=mock_db_session
+    )
+    mock_get_db_session.return_value.__exit__ = MagicMock(return_value=False)
+
+
+@patch(f"{_TASK_MODULE}.get_session_with_current_tenant")
+@patch(f"{_TASK_MODULE}.delete_chat_session")
+@patch(f"{_TASK_MODULE}.get_chat_sessions_older_than")
+@patch(f"{_TASK_MODULE}.mark_task_as_finished_with_id")
+@patch(f"{_TASK_MODULE}.register_task")
+def test_ttl_task_continues_after_session_delete_failure(
+    _mock_register: Any,
+    mock_mark_finished: MagicMock,
+    mock_get_old_sessions: MagicMock,
+    mock_delete_session: MagicMock,
+    mock_get_db_session: MagicMock,
+) -> None:
+    """One failing session should not prevent cleanup of remaining sessions."""
+    from ee.onyx.background.celery.tasks.ttl_management.tasks import (
+        perform_ttl_management_task,
+    )
+
+    user1, session1 = uuid4(), uuid4()
+    user2, session2 = uuid4(), uuid4()
+    user3, session3 = uuid4(), uuid4()
+
+    mock_get_old_sessions.return_value = [
+        (user1, session1),
+        (user2, session2),
+        (user3, session3),
+    ]
+
+    # Second session fails
+    mock_delete_session.side_effect = [
+        None,
+        RuntimeError("File does not exist"),
+        None,
+    ]
+
+    _setup_db_session_mock(mock_get_db_session)
+
+    mock_task = MagicMock()
+    mock_task.request.id = "test-task-id"
+
+    # Call the underlying function directly, bypassing Celery decorator
+    perform_ttl_management_task.__wrapped__(
+        mock_task, retention_limit_days=30, tenant_id="test"
+    )
+
+    # All three sessions should have been attempted
+    assert mock_delete_session.call_count == 3
+
+    # Task marked as finished with success=False (due to the one failure)
+    mock_mark_finished.assert_called()
+    finish_call_kwargs = mock_mark_finished.call_args[1]
+    assert finish_call_kwargs["success"] is False
+
+
+@patch(f"{_TASK_MODULE}.get_session_with_current_tenant")
+@patch(f"{_TASK_MODULE}.delete_chat_session")
+@patch(f"{_TASK_MODULE}.get_chat_sessions_older_than")
+@patch(f"{_TASK_MODULE}.mark_task_as_finished_with_id")
+@patch(f"{_TASK_MODULE}.register_task")
+def test_ttl_task_reports_success_when_all_deletions_pass(
+    _mock_register: Any,
+    mock_mark_finished: MagicMock,
+    mock_get_old_sessions: MagicMock,
+    mock_delete_session: MagicMock,
+    mock_get_db_session: MagicMock,
+) -> None:
+    """Task should report success when all sessions are deleted."""
+    from ee.onyx.background.celery.tasks.ttl_management.tasks import (
+        perform_ttl_management_task,
+    )
+
+    mock_get_old_sessions.return_value = [
+        (uuid4(), uuid4()),
+        (uuid4(), uuid4()),
+    ]
+    mock_delete_session.side_effect = None
+
+    _setup_db_session_mock(mock_get_db_session)
+
+    mock_task = MagicMock()
+    mock_task.request.id = "test-task-id"
+
+    perform_ttl_management_task.__wrapped__(
+        mock_task, retention_limit_days=30, tenant_id="test"
+    )
+
+    assert mock_delete_session.call_count == 2
+
+    mock_mark_finished.assert_called()
+    finish_call_kwargs = mock_mark_finished.call_args[1]
+    assert finish_call_kwargs["success"] is True

backend/tests/unit/onyx/connectors/canvas/test_canvas_connector.py

@@ -1,15 +1,23 @@
-"""Tests for Canvas connector — client (PR1)."""
+"""Tests for Canvas connector — client, credentials, conversion."""
 
+from datetime import datetime
+from datetime import timezone
 from typing import Any
 from unittest.mock import MagicMock
 from unittest.mock import patch
 
 import pytest
 
+from onyx.configs.constants import DocumentSource
 from onyx.connectors.canvas.client import CanvasApiClient
+from onyx.connectors.canvas.connector import CanvasConnector
+from onyx.connectors.exceptions import ConnectorValidationError
+from onyx.connectors.exceptions import CredentialExpiredError
+from onyx.connectors.exceptions import InsufficientPermissionsError
+from onyx.connectors.exceptions import UnexpectedValidationError
+from onyx.connectors.models import ConnectorMissingCredentialError
 from onyx.error_handling.exceptions import OnyxError
 
-
 # ---------------------------------------------------------------------------
 # Helpers
 # ---------------------------------------------------------------------------
@@ -18,6 +26,77 @@ FAKE_BASE_URL = "https://myschool.instructure.com"
 FAKE_TOKEN = "fake-canvas-token"
 
 
+def _mock_course(
+    course_id: int = 1,
+    name: str = "Intro to CS",
+    course_code: str = "CS101",
+) -> dict[str, Any]:
+    return {
+        "id": course_id,
+        "name": name,
+        "course_code": course_code,
+        "created_at": "2025-01-01T00:00:00Z",
+        "workflow_state": "available",
+    }
+
+
+def _build_connector(base_url: str = FAKE_BASE_URL) -> CanvasConnector:
+    """Build a connector with mocked credential validation."""
+    with patch("onyx.connectors.canvas.client.rl_requests") as mock_req:
+        mock_req.get.return_value = _mock_response(json_data=[_mock_course()])
+        connector = CanvasConnector(canvas_base_url=base_url)
+        connector.load_credentials({"canvas_access_token": FAKE_TOKEN})
+    return connector
+
+
+def _mock_page(
+    page_id: int = 10,
+    title: str = "Syllabus",
+    updated_at: str = "2025-06-01T12:00:00Z",
+) -> dict[str, Any]:
+    return {
+        "page_id": page_id,
+        "url": "syllabus",
+        "title": title,
+        "body": "<p>Welcome to the course</p>",
+        "created_at": "2025-01-15T00:00:00Z",
+        "updated_at": updated_at,
+    }
+
+
+def _mock_assignment(
+    assignment_id: int = 20,
+    name: str = "Homework 1",
+    course_id: int = 1,
+    updated_at: str = "2025-06-01T12:00:00Z",
+) -> dict[str, Any]:
+    return {
+        "id": assignment_id,
+        "name": name,
+        "description": "<p>Solve these problems</p>",
+        "html_url": f"{FAKE_BASE_URL}/courses/{course_id}/assignments/{assignment_id}",
+        "course_id": course_id,
+        "created_at": "2025-01-20T00:00:00Z",
+        "updated_at": updated_at,
+        "due_at": "2025-02-01T23:59:00Z",
+    }
+
+
+def _mock_announcement(
+    announcement_id: int = 30,
+    title: str = "Class Cancelled",
+    course_id: int = 1,
+    posted_at: str = "2025-06-01T12:00:00Z",
+) -> dict[str, Any]:
+    return {
+        "id": announcement_id,
+        "title": title,
+        "message": "<p>No class today</p>",
+        "html_url": f"{FAKE_BASE_URL}/courses/{course_id}/discussion_topics/{announcement_id}",
+        "posted_at": posted_at,
+    }
+
+
 def _mock_response(
     status_code: int = 200,
     json_data: Any = None,
@@ -325,6 +404,57 @@ class TestGet:
         assert result == expected
 
 
+# ---------------------------------------------------------------------------
+# CanvasApiClient.paginate tests
+# ---------------------------------------------------------------------------
+
+
+class TestPaginate:
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_single_page(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(
+            json_data=[{"id": 1}, {"id": 2}]
+        )
+        client = CanvasApiClient(
+            bearer_token=FAKE_TOKEN,
+            canvas_base_url=FAKE_BASE_URL,
+        )
+
+        pages = list(client.paginate("courses"))
+
+        assert len(pages) == 1
+        assert pages[0] == [{"id": 1}, {"id": 2}]
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_two_pages(self, mock_requests: MagicMock) -> None:
+        next_link = f'<{FAKE_BASE_URL}/api/v1/courses?page=2>; rel="next"'
+        page1 = _mock_response(json_data=[{"id": 1}], link_header=next_link)
+        page2 = _mock_response(json_data=[{"id": 2}])
+        mock_requests.get.side_effect = [page1, page2]
+        client = CanvasApiClient(
+            bearer_token=FAKE_TOKEN,
+            canvas_base_url=FAKE_BASE_URL,
+        )
+
+        pages = list(client.paginate("courses"))
+
+        assert len(pages) == 2
+        assert pages[0] == [{"id": 1}]
+        assert pages[1] == [{"id": 2}]
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_empty_response(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(json_data=[])
+        client = CanvasApiClient(
+            bearer_token=FAKE_TOKEN,
+            canvas_base_url=FAKE_BASE_URL,
+        )
+
+        pages = list(client.paginate("courses"))
+
+        assert pages == []
+
+
 # ---------------------------------------------------------------------------
 # CanvasApiClient._parse_next_link tests
 # ---------------------------------------------------------------------------
@@ -379,3 +509,368 @@ class TestParseNextLink:
 
         with pytest.raises(OnyxError, match="must use https"):
             self.client._parse_next_link(header)
+
+
+# ---------------------------------------------------------------------------
+# CanvasConnector — credential loading
+# ---------------------------------------------------------------------------
+
+
+class TestLoadCredentials:
+    def _assert_load_credentials_raises(
+        self,
+        status_code: int,
+        expected_error: type[Exception],
+        mock_requests: MagicMock,
+    ) -> None:
+        """Helper: assert load_credentials raises expected_error for a given status."""
+        mock_requests.get.return_value = _mock_response(status_code, {})
+        connector = CanvasConnector(canvas_base_url=FAKE_BASE_URL)
+        with pytest.raises(expected_error):
+            connector.load_credentials({"canvas_access_token": FAKE_TOKEN})
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_load_credentials_success(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(json_data=[_mock_course()])
+        connector = CanvasConnector(canvas_base_url=FAKE_BASE_URL)
+
+        result = connector.load_credentials({"canvas_access_token": FAKE_TOKEN})
+
+        assert result is None
+        assert connector._canvas_client is not None
+
+    def test_canvas_client_raises_without_credentials(self) -> None:
+        connector = CanvasConnector(canvas_base_url=FAKE_BASE_URL)
+
+        with pytest.raises(ConnectorMissingCredentialError):
+            _ = connector.canvas_client
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_load_credentials_invalid_token(self, mock_requests: MagicMock) -> None:
+        self._assert_load_credentials_raises(401, CredentialExpiredError, mock_requests)
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_load_credentials_insufficient_permissions(
+        self, mock_requests: MagicMock
+    ) -> None:
+        self._assert_load_credentials_raises(
+            403, InsufficientPermissionsError, mock_requests
+        )
+
+
+# ---------------------------------------------------------------------------
+# CanvasConnector — URL normalization
+# ---------------------------------------------------------------------------
+
+
+class TestConnectorUrlNormalization:
+    def test_strips_api_v1_suffix(self) -> None:
+        connector = _build_connector(base_url=f"{FAKE_BASE_URL}/api/v1")
+
+        result = connector.canvas_base_url
+        expected = FAKE_BASE_URL
+
+        assert result == expected
+
+    def test_strips_trailing_slash(self) -> None:
+        connector = _build_connector(base_url=f"{FAKE_BASE_URL}/")
+
+        result = connector.canvas_base_url
+        expected = FAKE_BASE_URL
+
+        assert result == expected
+
+    def test_no_change_for_clean_url(self) -> None:
+        connector = _build_connector(base_url=FAKE_BASE_URL)
+
+        result = connector.canvas_base_url
+        expected = FAKE_BASE_URL
+
+        assert result == expected
+
+
+# ---------------------------------------------------------------------------
+# CanvasConnector — document conversion
+# ---------------------------------------------------------------------------
+
+
+class TestDocumentConversion:
+    def setup_method(self) -> None:
+        self.connector = _build_connector()
+
+    def test_convert_page_to_document(self) -> None:
+        from onyx.connectors.canvas.connector import CanvasPage
+
+        page = CanvasPage(
+            page_id=10,
+            url="syllabus",
+            title="Syllabus",
+            body="<p>Welcome</p>",
+            created_at="2025-01-15T00:00:00Z",
+            updated_at="2025-06-01T12:00:00Z",
+            course_id=1,
+        )
+
+        doc = self.connector._convert_page_to_document(page)
+
+        expected_id = "canvas-page-1-10"
+        expected_metadata = {"course_id": "1", "type": "page"}
+        expected_updated_at = datetime(2025, 6, 1, 12, 0, tzinfo=timezone.utc)
+
+        assert doc.id == expected_id
+        assert doc.source == DocumentSource.CANVAS
+        assert doc.semantic_identifier == "Syllabus"
+        assert doc.metadata == expected_metadata
+        assert doc.sections[0].link is not None
+        assert f"{FAKE_BASE_URL}/courses/1/pages/syllabus" in doc.sections[0].link
+        assert doc.doc_updated_at == expected_updated_at
+
+    def test_convert_page_without_body(self) -> None:
+        from onyx.connectors.canvas.connector import CanvasPage
+
+        page = CanvasPage(
+            page_id=11,
+            url="empty-page",
+            title="Empty Page",
+            body=None,
+            created_at="2025-01-15T00:00:00Z",
+            updated_at="2025-06-01T12:00:00Z",
+            course_id=1,
+        )
+
+        doc = self.connector._convert_page_to_document(page)
+        section_text = doc.sections[0].text
+        assert section_text is not None
+
+        assert "Empty Page" in section_text
+        assert "<p>" not in section_text
+
+    def test_convert_assignment_to_document(self) -> None:
+        from onyx.connectors.canvas.connector import CanvasAssignment
+
+        assignment = CanvasAssignment(
+            id=20,
+            name="Homework 1",
+            description="<p>Solve these</p>",
+            html_url=f"{FAKE_BASE_URL}/courses/1/assignments/20",
+            course_id=1,
+            created_at="2025-01-20T00:00:00Z",
+            updated_at="2025-06-01T12:00:00Z",
+            due_at="2025-02-01T23:59:00Z",
+        )
+
+        doc = self.connector._convert_assignment_to_document(assignment)
+
+        expected_id = "canvas-assignment-1-20"
+        expected_due_text = "Due: February 01, 2025 23:59 UTC"
+
+        assert doc.id == expected_id
+        assert doc.source == DocumentSource.CANVAS
+        assert doc.semantic_identifier == "Homework 1"
+        assert doc.sections[0].text is not None
+        assert expected_due_text in doc.sections[0].text
+
+    def test_convert_assignment_without_description(self) -> None:
+        from onyx.connectors.canvas.connector import CanvasAssignment
+
+        assignment = CanvasAssignment(
+            id=21,
+            name="Quiz 1",
+            description=None,
+            html_url=f"{FAKE_BASE_URL}/courses/1/assignments/21",
+            course_id=1,
+            created_at="2025-01-20T00:00:00Z",
+            updated_at="2025-06-01T12:00:00Z",
+            due_at=None,
+        )
+
+        doc = self.connector._convert_assignment_to_document(assignment)
+        section_text = doc.sections[0].text
+        assert section_text is not None
+
+        assert "Quiz 1" in section_text
+        assert "Due:" not in section_text
+
+    def test_convert_announcement_to_document(self) -> None:
+        from onyx.connectors.canvas.connector import CanvasAnnouncement
+
+        announcement = CanvasAnnouncement(
+            id=30,
+            title="Class Cancelled",
+            message="<p>No class today</p>",
+            html_url=f"{FAKE_BASE_URL}/courses/1/discussion_topics/30",
+            posted_at="2025-06-01T12:00:00Z",
+            course_id=1,
+        )
+
+        doc = self.connector._convert_announcement_to_document(announcement)
+
+        expected_id = "canvas-announcement-1-30"
+        expected_updated_at = datetime(2025, 6, 1, 12, 0, tzinfo=timezone.utc)
+
+        assert doc.id == expected_id
+        assert doc.source == DocumentSource.CANVAS
+        assert doc.semantic_identifier == "Class Cancelled"
+        assert doc.doc_updated_at == expected_updated_at
+
+    def test_convert_announcement_without_posted_at(self) -> None:
+        from onyx.connectors.canvas.connector import CanvasAnnouncement
+
+        announcement = CanvasAnnouncement(
+            id=31,
+            title="TBD Announcement",
+            message=None,
+            html_url=f"{FAKE_BASE_URL}/courses/1/discussion_topics/31",
+            posted_at=None,
+            course_id=1,
+        )
+
+        doc = self.connector._convert_announcement_to_document(announcement)
+
+        assert doc.doc_updated_at is None
+
+
+# ---------------------------------------------------------------------------
+# CanvasConnector — validate_connector_settings
+# ---------------------------------------------------------------------------
+
+
+class TestValidateConnectorSettings:
+    def _assert_validate_raises(
+        self,
+        status_code: int,
+        expected_error: type[Exception],
+        mock_requests: MagicMock,
+    ) -> None:
+        """Helper: assert validate_connector_settings raises expected_error."""
+        success_resp = _mock_response(json_data=[_mock_course()])
+        fail_resp = _mock_response(status_code, {})
+        mock_requests.get.side_effect = [success_resp, fail_resp]
+        connector = CanvasConnector(canvas_base_url=FAKE_BASE_URL)
+        connector.load_credentials({"canvas_access_token": FAKE_TOKEN})
+        with pytest.raises(expected_error):
+            connector.validate_connector_settings()
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_validate_success(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(json_data=[_mock_course()])
+        connector = _build_connector()
+
+        connector.validate_connector_settings()  # should not raise
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_validate_expired_credential(self, mock_requests: MagicMock) -> None:
+        self._assert_validate_raises(401, CredentialExpiredError, mock_requests)
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_validate_insufficient_permissions(self, mock_requests: MagicMock) -> None:
+        self._assert_validate_raises(403, InsufficientPermissionsError, mock_requests)
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_validate_rate_limited(self, mock_requests: MagicMock) -> None:
+        self._assert_validate_raises(429, ConnectorValidationError, mock_requests)
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_validate_unexpected_error(self, mock_requests: MagicMock) -> None:
+        self._assert_validate_raises(500, UnexpectedValidationError, mock_requests)
+
+
+# ---------------------------------------------------------------------------
+# _list_* pagination tests
+# ---------------------------------------------------------------------------
+
+
+class TestListCourses:
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_single_page(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(
+            json_data=[_mock_course(1), _mock_course(2, "CS201", "Data Structures")]
+        )
+        connector = _build_connector()
+
+        result = connector._list_courses()
+
+        assert len(result) == 2
+        assert result[0].id == 1
+        assert result[1].id == 2
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_empty_response(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(json_data=[])
+        connector = _build_connector()
+
+        result = connector._list_courses()
+
+        assert result == []
+
+
+class TestListPages:
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_single_page(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(
+            json_data=[_mock_page(10), _mock_page(11, "Notes")]
+        )
+        connector = _build_connector()
+
+        result = connector._list_pages(course_id=1)
+
+        assert len(result) == 2
+        assert result[0].page_id == 10
+        assert result[1].page_id == 11
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_empty_response(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(json_data=[])
+        connector = _build_connector()
+
+        result = connector._list_pages(course_id=1)
+
+        assert result == []
+
+
+class TestListAssignments:
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_single_page(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(
+            json_data=[_mock_assignment(20), _mock_assignment(21, "Quiz 1")]
+        )
+        connector = _build_connector()
+
+        result = connector._list_assignments(course_id=1)
+
+        assert len(result) == 2
+        assert result[0].id == 20
+        assert result[1].id == 21
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_empty_response(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(json_data=[])
+        connector = _build_connector()
+
+        result = connector._list_assignments(course_id=1)
+
+        assert result == []
+
+
+class TestListAnnouncements:
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_single_page(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(
+            json_data=[_mock_announcement(30), _mock_announcement(31, "Update")]
+        )
+        connector = _build_connector()
+
+        result = connector._list_announcements(course_id=1)
+
+        assert len(result) == 2
+        assert result[0].id == 30
+        assert result[1].id == 31
+
+    @patch("onyx.connectors.canvas.client.rl_requests")
+    def test_empty_response(self, mock_requests: MagicMock) -> None:
+        mock_requests.get.return_value = _mock_response(json_data=[])
+        connector = _build_connector()
+
+        result = connector._list_announcements(course_id=1)
+
+        assert result == []

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

@@ -0,0 +1,58 @@
+"""Tests for chat session and message deletion resilience."""
+
+from typing import Any
+from unittest.mock import MagicMock
+from unittest.mock import patch
+from uuid import uuid4
+
+from onyx.db.chat import delete_messages_and_files_from_chat_session
+
+
+@patch("onyx.db.chat.delete_orphaned_search_docs")
+@patch("onyx.db.chat.get_default_file_store")
+def test_delete_messages_skips_missing_files(
+    mock_get_file_store: MagicMock,
+    _mock_delete_orphaned: Any,
+) -> None:
+    """Deletion should continue when a referenced file record no longer exists."""
+    session_id = uuid4()
+
+    file_store = MagicMock()
+    file_store.delete_file.side_effect = [
+        None,  # first file deletes fine
+        RuntimeError("File by id abc does not exist or was deleted"),
+        None,  # third file deletes fine
+    ]
+    mock_get_file_store.return_value = file_store
+
+    mock_db_session = MagicMock()
+    mock_db_session.execute.return_value.fetchall.return_value = [
+        (1, [{"id": "file-ok-1"}, {"id": "file-missing"}, {"id": "file-ok-2"}]),
+    ]
+
+    delete_messages_and_files_from_chat_session(session_id, mock_db_session)
+
+    assert file_store.delete_file.call_count == 3
+    mock_db_session.execute.assert_called()
+    mock_db_session.commit.assert_called()
+
+
+@patch("onyx.db.chat.delete_orphaned_search_docs")
+@patch("onyx.db.chat.get_default_file_store")
+def test_delete_messages_succeeds_with_no_files(
+    mock_get_file_store: MagicMock,
+    _mock_delete_orphaned: Any,
+) -> None:
+    """Deletion works when messages have no attached files."""
+    session_id = uuid4()
+
+    mock_db_session = MagicMock()
+    mock_db_session.execute.return_value.fetchall.return_value = [
+        (1, None),
+        (2, []),
+    ]
+
+    delete_messages_and_files_from_chat_session(session_id, mock_db_session)
+
+    mock_get_file_store.return_value.delete_file.assert_not_called()
+    mock_db_session.commit.assert_called()

backend/tests/unit/onyx/document_index/opensearch/test_opensearch_batch_flush.py

@@ -0,0 +1,223 @@
+from unittest.mock import MagicMock
+from unittest.mock import patch
+
+from onyx.access.models import DocumentAccess
+from onyx.configs.constants import DocumentSource
+from onyx.connectors.models import Document
+from onyx.connectors.models import TextSection
+from onyx.document_index.interfaces_new import IndexingMetadata
+from onyx.document_index.interfaces_new import TenantState
+from onyx.document_index.opensearch.opensearch_document_index import (
+    OpenSearchDocumentIndex,
+)
+from onyx.indexing.models import ChunkEmbedding
+from onyx.indexing.models import DocMetadataAwareIndexChunk
+
+
+def _make_chunk(
+    doc_id: str,
+    chunk_id: int,
+) -> DocMetadataAwareIndexChunk:
+    """Creates a minimal DocMetadataAwareIndexChunk for testing."""
+    doc = Document(
+        id=doc_id,
+        sections=[TextSection(text="test", link="http://test.com")],
+        source=DocumentSource.FILE,
+        semantic_identifier="test_doc",
+        metadata={},
+    )
+    access = DocumentAccess.build(
+        user_emails=[],
+        user_groups=[],
+        external_user_emails=[],
+        external_user_group_ids=[],
+        is_public=True,
+    )
+    return DocMetadataAwareIndexChunk(
+        chunk_id=chunk_id,
+        blurb="test",
+        content="test content",
+        source_links={0: "http://test.com"},
+        image_file_id=None,
+        section_continuation=False,
+        source_document=doc,
+        title_prefix="",
+        metadata_suffix_semantic="",
+        metadata_suffix_keyword="",
+        mini_chunk_texts=None,
+        large_chunk_id=None,
+        doc_summary="",
+        chunk_context="",
+        contextual_rag_reserved_tokens=0,
+        embeddings=ChunkEmbedding(full_embedding=[0.1] * 10, mini_chunk_embeddings=[]),
+        title_embedding=[0.1] * 10,
+        tenant_id="test_tenant",
+        access=access,
+        document_sets=set(),
+        user_project=[],
+        personas=[],
+        boost=0,
+        aggregated_chunk_boost_factor=1.0,
+        ancestor_hierarchy_node_ids=[],
+    )
+
+
+def _make_index() -> tuple[OpenSearchDocumentIndex, MagicMock]:
+    """Creates an OpenSearchDocumentIndex with a mocked client.
+    Returns the index and the mock for bulk_index_documents."""
+    mock_client = MagicMock()
+    mock_bulk = MagicMock()
+    mock_client.bulk_index_documents = mock_bulk
+
+    tenant_state = TenantState(tenant_id="test_tenant", multitenant=False)
+
+    index = OpenSearchDocumentIndex.__new__(OpenSearchDocumentIndex)
+    index._index_name = "test_index"
+    index._client = mock_client
+    index._tenant_state = tenant_state
+
+    return index, mock_bulk
+
+
+def _make_metadata(doc_id: str, chunk_count: int) -> IndexingMetadata:
+    return IndexingMetadata(
+        doc_id_to_chunk_cnt_diff={
+            doc_id: IndexingMetadata.ChunkCounts(
+                old_chunk_cnt=0,
+                new_chunk_cnt=chunk_count,
+            ),
+        },
+    )
+
+
+@patch(
+    "onyx.document_index.opensearch.opensearch_document_index.MAX_CHUNKS_PER_DOC_BATCH",
+    100,
+)
+def test_single_doc_under_batch_limit_flushes_once() -> None:
+    """A document with fewer chunks than MAX_CHUNKS_PER_DOC_BATCH should flush once."""
+    index, mock_bulk = _make_index()
+    doc_id = "doc_1"
+    num_chunks = 50
+    chunks = [_make_chunk(doc_id, i) for i in range(num_chunks)]
+    metadata = _make_metadata(doc_id, num_chunks)
+
+    with patch.object(index, "delete", return_value=0):
+        index.index(chunks, metadata)
+
+    assert mock_bulk.call_count == 1
+    batch_arg = mock_bulk.call_args_list[0]
+    assert len(batch_arg.kwargs["documents"]) == num_chunks
+
+
+@patch(
+    "onyx.document_index.opensearch.opensearch_document_index.MAX_CHUNKS_PER_DOC_BATCH",
+    100,
+)
+def test_single_doc_over_batch_limit_flushes_multiple_times() -> None:
+    """A document with more chunks than MAX_CHUNKS_PER_DOC_BATCH should flush multiple times."""
+    index, mock_bulk = _make_index()
+    doc_id = "doc_1"
+    num_chunks = 250
+    chunks = [_make_chunk(doc_id, i) for i in range(num_chunks)]
+    metadata = _make_metadata(doc_id, num_chunks)
+
+    with patch.object(index, "delete", return_value=0):
+        index.index(chunks, metadata)
+
+    # 250 chunks / 100 per batch = 3 flushes (100 + 100 + 50)
+    assert mock_bulk.call_count == 3
+    batch_sizes = [len(call.kwargs["documents"]) for call in mock_bulk.call_args_list]
+    assert batch_sizes == [100, 100, 50]
+
+
+@patch(
+    "onyx.document_index.opensearch.opensearch_document_index.MAX_CHUNKS_PER_DOC_BATCH",
+    100,
+)
+def test_single_doc_exactly_at_batch_limit() -> None:
+    """A document with exactly MAX_CHUNKS_PER_DOC_BATCH chunks should flush once
+    (the flush happens on the next chunk, not at the boundary)."""
+    index, mock_bulk = _make_index()
+    doc_id = "doc_1"
+    num_chunks = 100
+    chunks = [_make_chunk(doc_id, i) for i in range(num_chunks)]
+    metadata = _make_metadata(doc_id, num_chunks)
+
+    with patch.object(index, "delete", return_value=0):
+        index.index(chunks, metadata)
+
+    # 100 chunks hit the >= check on chunk 101 which doesn't exist,
+    # so final flush handles all 100
+    # Actually: the elif fires when len(current_chunks) >= 100, which happens
+    # when current_chunks has 100 items and the 101st chunk arrives.
+    # With exactly 100 chunks, the 100th chunk makes len == 99, then appended -> 100.
+    # No 101st chunk arrives, so the final flush handles all 100.
+    assert mock_bulk.call_count == 1
+
+
+@patch(
+    "onyx.document_index.opensearch.opensearch_document_index.MAX_CHUNKS_PER_DOC_BATCH",
+    100,
+)
+def test_single_doc_one_over_batch_limit() -> None:
+    """101 chunks for one doc: first 100 flushed when the 101st arrives, then
+    the 101st is flushed at the end."""
+    index, mock_bulk = _make_index()
+    doc_id = "doc_1"
+    num_chunks = 101
+    chunks = [_make_chunk(doc_id, i) for i in range(num_chunks)]
+    metadata = _make_metadata(doc_id, num_chunks)
+
+    with patch.object(index, "delete", return_value=0):
+        index.index(chunks, metadata)
+
+    assert mock_bulk.call_count == 2
+    batch_sizes = [len(call.kwargs["documents"]) for call in mock_bulk.call_args_list]
+    assert batch_sizes == [100, 1]
+
+
+@patch(
+    "onyx.document_index.opensearch.opensearch_document_index.MAX_CHUNKS_PER_DOC_BATCH",
+    100,
+)
+def test_multiple_docs_each_under_limit_flush_per_doc() -> None:
+    """Multiple documents each under the batch limit should flush once per document."""
+    index, mock_bulk = _make_index()
+    chunks = []
+    for doc_idx in range(3):
+        doc_id = f"doc_{doc_idx}"
+        for chunk_idx in range(50):
+            chunks.append(_make_chunk(doc_id, chunk_idx))
+
+    metadata = IndexingMetadata(
+        doc_id_to_chunk_cnt_diff={
+            f"doc_{i}": IndexingMetadata.ChunkCounts(old_chunk_cnt=0, new_chunk_cnt=50)
+            for i in range(3)
+        },
+    )
+
+    with patch.object(index, "delete", return_value=0):
+        index.index(chunks, metadata)
+
+    # 3 documents = 3 flushes (one per doc boundary + final)
+    assert mock_bulk.call_count == 3
+
+
+@patch(
+    "onyx.document_index.opensearch.opensearch_document_index.MAX_CHUNKS_PER_DOC_BATCH",
+    100,
+)
+def test_delete_called_once_per_document() -> None:
+    """Even with multiple flushes for a single document, delete should only be
+    called once per document."""
+    index, _mock_bulk = _make_index()
+    doc_id = "doc_1"
+    num_chunks = 250
+    chunks = [_make_chunk(doc_id, i) for i in range(num_chunks)]
+    metadata = _make_metadata(doc_id, num_chunks)
+
+    with patch.object(index, "delete", return_value=0) as mock_delete:
+        index.index(chunks, metadata)
+
+    mock_delete.assert_called_once_with(doc_id, None)

backend/tests/unit/onyx/document_index/vespa/test_vespa_batch_flush.py

@@ -0,0 +1,152 @@
+"""Unit tests for VespaDocumentIndex.index().
+
+These tests mock all external I/O (HTTP calls, thread pools) and verify
+the streaming logic, ID cleaning/mapping, and DocumentInsertionRecord
+construction.
+"""
+
+from unittest.mock import MagicMock
+from unittest.mock import patch
+
+from onyx.access.models import DocumentAccess
+from onyx.configs.constants import DocumentSource
+from onyx.connectors.models import Document
+from onyx.connectors.models import TextSection
+from onyx.document_index.interfaces import EnrichedDocumentIndexingInfo
+from onyx.document_index.interfaces_new import IndexingMetadata
+from onyx.document_index.interfaces_new import TenantState
+from onyx.document_index.vespa.vespa_document_index import VespaDocumentIndex
+from onyx.indexing.models import ChunkEmbedding
+from onyx.indexing.models import DocMetadataAwareIndexChunk
+from onyx.indexing.models import IndexChunk
+
+
+def _make_chunk(
+    doc_id: str,
+    chunk_id: int = 0,
+    content: str = "test content",
+) -> DocMetadataAwareIndexChunk:
+    doc = Document(
+        id=doc_id,
+        semantic_identifier="test_doc",
+        sections=[TextSection(text=content, link=None)],
+        source=DocumentSource.NOT_APPLICABLE,
+        metadata={},
+    )
+    index_chunk = IndexChunk(
+        chunk_id=chunk_id,
+        blurb=content[:50],
+        content=content,
+        source_links=None,
+        image_file_id=None,
+        section_continuation=False,
+        source_document=doc,
+        title_prefix="",
+        metadata_suffix_semantic="",
+        metadata_suffix_keyword="",
+        contextual_rag_reserved_tokens=0,
+        doc_summary="",
+        chunk_context="",
+        mini_chunk_texts=None,
+        large_chunk_id=None,
+        embeddings=ChunkEmbedding(
+            full_embedding=[0.1] * 10,
+            mini_chunk_embeddings=[],
+        ),
+        title_embedding=None,
+    )
+    access = DocumentAccess.build(
+        user_emails=[],
+        user_groups=[],
+        external_user_emails=[],
+        external_user_group_ids=[],
+        is_public=True,
+    )
+    return DocMetadataAwareIndexChunk.from_index_chunk(
+        index_chunk=index_chunk,
+        access=access,
+        document_sets=set(),
+        user_project=[],
+        personas=[],
+        boost=0,
+        aggregated_chunk_boost_factor=1.0,
+        tenant_id="test_tenant",
+    )
+
+
+def _make_indexing_metadata(
+    doc_ids: list[str],
+    old_counts: list[int],
+    new_counts: list[int],
+) -> IndexingMetadata:
+    return IndexingMetadata(
+        doc_id_to_chunk_cnt_diff={
+            doc_id: IndexingMetadata.ChunkCounts(
+                old_chunk_cnt=old,
+                new_chunk_cnt=new,
+            )
+            for doc_id, old, new in zip(doc_ids, old_counts, new_counts)
+        }
+    )
+
+
+def _stub_enrich(
+    doc_id: str,
+    old_chunk_cnt: int,
+) -> EnrichedDocumentIndexingInfo:
+    """Build an EnrichedDocumentIndexingInfo that says 'no chunks to delete'
+    when old_chunk_cnt == 0, or 'has existing chunks' otherwise."""
+    return EnrichedDocumentIndexingInfo(
+        doc_id=doc_id,
+        chunk_start_index=0,
+        old_version=False,
+        chunk_end_index=old_chunk_cnt,
+    )
+
+
+@patch("onyx.document_index.vespa.vespa_document_index.batch_index_vespa_chunks")
+@patch("onyx.document_index.vespa.vespa_document_index.delete_vespa_chunks")
+@patch(
+    "onyx.document_index.vespa.vespa_document_index.get_document_chunk_ids",
+    return_value=[],
+)
+@patch("onyx.document_index.vespa.vespa_document_index._enrich_basic_chunk_info")
+@patch(
+    "onyx.document_index.vespa.vespa_document_index.BATCH_SIZE",
+    3,
+)
+def test_index_respects_batch_size(
+    mock_enrich: MagicMock,
+    mock_get_chunk_ids: MagicMock,  # noqa: ARG001
+    mock_delete: MagicMock,  # noqa: ARG001
+    mock_batch_index: MagicMock,
+) -> None:
+    """When chunks exceed BATCH_SIZE, batch_index_vespa_chunks is called
+    multiple times with correctly sized batches."""
+    mock_enrich.return_value = _stub_enrich("doc1", old_chunk_cnt=0)
+
+    index = VespaDocumentIndex(
+        index_name="test_index",
+        tenant_state=TenantState(tenant_id="test_tenant", multitenant=False),
+        large_chunks_enabled=False,
+        httpx_client=MagicMock(),
+    )
+
+    chunks = [_make_chunk("doc1", chunk_id=i) for i in range(7)]
+    metadata = _make_indexing_metadata(["doc1"], old_counts=[0], new_counts=[7])
+
+    results = index.index(chunks=chunks, indexing_metadata=metadata)
+
+    assert len(results) == 1
+
+    # With BATCH_SIZE=3 and 7 chunks: batches of 3, 3, 1
+    assert mock_batch_index.call_count == 3
+    batch_sizes = [len(c.kwargs["chunks"]) for c in mock_batch_index.call_args_list]
+    assert batch_sizes == [3, 3, 1]
+
+    # Verify all chunks are accounted for and in order
+    all_indexed = [
+        chunk for c in mock_batch_index.call_args_list for chunk in c.kwargs["chunks"]
+    ]
+    assert len(all_indexed) == 7
+    assert [c.chunk_id for c in all_indexed] == list(range(7))

backend/tests/unit/onyx/indexing/test_embed_chunks_in_batches.py

@@ -0,0 +1,391 @@
+"""Unit tests for _embed_chunks_to_store.
+
+Tests cover:
+  - Single batch, no failures
+  - Multiple batches, no failures
+  - Failure in a single batch
+  - Cross-batch document failure scrubbing
+  - Later batches skip already-failed docs
+  - Empty input
+  - All chunks fail
+"""
+
+from collections.abc import Callable
+from unittest.mock import MagicMock
+from unittest.mock import patch
+
+from onyx.connectors.models import ConnectorFailure
+from onyx.connectors.models import Document
+from onyx.connectors.models import DocumentFailure
+from onyx.connectors.models import DocumentSource
+from onyx.connectors.models import TextSection
+from onyx.indexing.chunk_batch_store import ChunkBatchStore
+from onyx.indexing.indexing_pipeline import _embed_chunks_to_store
+from onyx.indexing.models import ChunkEmbedding
+from onyx.indexing.models import DocAwareChunk
+from onyx.indexing.models import IndexChunk
+
+
+def _make_doc(doc_id: str) -> Document:
+    return Document(
+        id=doc_id,
+        semantic_identifier="test",
+        source=DocumentSource.FILE,
+        sections=[TextSection(text="test", link=None)],
+        metadata={},
+    )
+
+
+def _make_chunk(doc_id: str, chunk_id: int) -> DocAwareChunk:
+    return DocAwareChunk(
+        chunk_id=chunk_id,
+        blurb="test",
+        content="test content",
+        source_links=None,
+        image_file_id=None,
+        section_continuation=False,
+        source_document=_make_doc(doc_id),
+        title_prefix="",
+        metadata_suffix_semantic="",
+        metadata_suffix_keyword="",
+        mini_chunk_texts=None,
+        large_chunk_id=None,
+        doc_summary="",
+        chunk_context="",
+        contextual_rag_reserved_tokens=0,
+    )
+
+
+def _make_index_chunk(doc_id: str, chunk_id: int) -> IndexChunk:
+    """Create an IndexChunk (a DocAwareChunk with embeddings)."""
+    return IndexChunk(
+        chunk_id=chunk_id,
+        blurb="test",
+        content="test content",
+        source_links=None,
+        image_file_id=None,
+        section_continuation=False,
+        source_document=_make_doc(doc_id),
+        title_prefix="",
+        metadata_suffix_semantic="",
+        metadata_suffix_keyword="",
+        mini_chunk_texts=None,
+        large_chunk_id=None,
+        doc_summary="",
+        chunk_context="",
+        contextual_rag_reserved_tokens=0,
+        embeddings=ChunkEmbedding(
+            full_embedding=[0.1] * 10,
+            mini_chunk_embeddings=[],
+        ),
+        title_embedding=None,
+    )
+
+
+def _make_failure(doc_id: str) -> ConnectorFailure:
+    return ConnectorFailure(
+        failed_document=DocumentFailure(document_id=doc_id, document_link=None),
+        failure_message="embedding failed",
+        exception=RuntimeError("embedding failed"),
+    )
+
+
+def _mock_embed_success(
+    chunks: list[DocAwareChunk], **_kwargs: object
+) -> tuple[list[IndexChunk], list[ConnectorFailure]]:
+    """Simulate successful embedding of all chunks."""
+    return (
+        [_make_index_chunk(c.source_document.id, c.chunk_id) for c in chunks],
+        [],
+    )
+
+
+def _mock_embed_fail_doc(
+    fail_doc_id: str,
+) -> Callable[..., tuple[list[IndexChunk], list[ConnectorFailure]]]:
+    """Return an embed mock that fails all chunks for a specific doc."""
+
+    def _embed(
+        chunks: list[DocAwareChunk], **_kwargs: object
+    ) -> tuple[list[IndexChunk], list[ConnectorFailure]]:
+        successes = [
+            _make_index_chunk(c.source_document.id, c.chunk_id)
+            for c in chunks
+            if c.source_document.id != fail_doc_id
+        ]
+        failures = (
+            [_make_failure(fail_doc_id)]
+            if any(c.source_document.id == fail_doc_id for c in chunks)
+            else []
+        )
+        return successes, failures
+
+    return _embed
+
+
+class TestEmbedChunksInBatches:
+    @patch(
+        "onyx.indexing.indexing_pipeline.embed_chunks_with_failure_handling",
+    )
+    @patch("onyx.indexing.indexing_pipeline.MAX_CHUNKS_PER_DOC_BATCH", 100)
+    def test_single_batch_no_failures(self, mock_embed: MagicMock) -> None:
+        """All chunks fit in one batch and embed successfully."""
+        mock_embed.side_effect = _mock_embed_success
+
+        with ChunkBatchStore() as store:
+            chunks = [_make_chunk("doc1", i) for i in range(3)]
+            result = _embed_chunks_to_store(
+                chunks=chunks,
+                embedder=MagicMock(),
+                tenant_id="test",
+                request_id=None,
+                store=store,
+            )
+
+            assert len(result.successful_chunk_ids) == 3
+            assert len(result.connector_failures) == 0
+
+            # Verify stored contents
+            assert len(store._batch_files()) == 1
+            stored = list(store.stream())
+            assert len(stored) == 3
+
+    @patch(
+        "onyx.indexing.indexing_pipeline.embed_chunks_with_failure_handling",
+    )
+    @patch("onyx.indexing.indexing_pipeline.MAX_CHUNKS_PER_DOC_BATCH", 3)
+    def test_multiple_batches_no_failures(self, mock_embed: MagicMock) -> None:
+        """Chunks are split across multiple batches, all succeed."""
+        mock_embed.side_effect = _mock_embed_success
+
+        with ChunkBatchStore() as store:
+            chunks = [_make_chunk("doc1", i) for i in range(7)]
+            result = _embed_chunks_to_store(
+                chunks=chunks,
+                embedder=MagicMock(),
+                tenant_id="test",
+                request_id=None,
+                store=store,
+            )
+
+            assert len(result.successful_chunk_ids) == 7
+            assert len(result.connector_failures) == 0
+            assert len(store._batch_files()) == 3  # 3 + 3 + 1
+
+    @patch(
+        "onyx.indexing.indexing_pipeline.embed_chunks_with_failure_handling",
+    )
+    @patch("onyx.indexing.indexing_pipeline.MAX_CHUNKS_PER_DOC_BATCH", 100)
+    def test_single_batch_with_failure(self, mock_embed: MagicMock) -> None:
+        """One doc fails embedding, its chunks are excluded from results."""
+        mock_embed.side_effect = _mock_embed_fail_doc("doc2")
+
+        with ChunkBatchStore() as store:
+            chunks = [
+                _make_chunk("doc1", 0),
+                _make_chunk("doc2", 1),
+                _make_chunk("doc1", 2),
+            ]
+            result = _embed_chunks_to_store(
+                chunks=chunks,
+                embedder=MagicMock(),
+                tenant_id="test",
+                request_id=None,
+                store=store,
+            )
+
+            assert len(result.connector_failures) == 1
+            successful_doc_ids = {doc_id for _, doc_id in result.successful_chunk_ids}
+            assert "doc2" not in successful_doc_ids
+            assert "doc1" in successful_doc_ids
+
+    @patch(
+        "onyx.indexing.indexing_pipeline.embed_chunks_with_failure_handling",
+    )
+    @patch("onyx.indexing.indexing_pipeline.MAX_CHUNKS_PER_DOC_BATCH", 3)
+    def test_cross_batch_failure_scrubs_earlier_batch(
+        self, mock_embed: MagicMock
+    ) -> None:
+        """Doc A spans batches 0 and 1.  It succeeds in batch 0 but fails in
+        batch 1.  Its chunks should be scrubbed from batch 0's batch file."""
+        call_count = 0
+
+        def _embed(
+            chunks: list[DocAwareChunk], **_kwargs: object
+        ) -> tuple[list[IndexChunk], list[ConnectorFailure]]:
+            nonlocal call_count
+            call_count += 1
+            if call_count == 1:
+                return _mock_embed_success(chunks)
+            else:
+                return _mock_embed_fail_doc("docA")(chunks)
+
+        mock_embed.side_effect = _embed
+
+        with ChunkBatchStore() as store:
+            chunks = [
+                _make_chunk("docA", 0),
+                _make_chunk("docA", 1),
+                _make_chunk("docA", 2),
+                _make_chunk("docA", 3),
+                _make_chunk("docB", 0),
+                _make_chunk("docB", 1),
+            ]
+            result = _embed_chunks_to_store(
+                chunks=chunks,
+                embedder=MagicMock(),
+                tenant_id="test",
+                request_id=None,
+                store=store,
+            )
+
+            # docA should be fully excluded from results
+            successful_doc_ids = {doc_id for _, doc_id in result.successful_chunk_ids}
+            assert "docA" not in successful_doc_ids
+            assert "docB" in successful_doc_ids
+            assert len(result.connector_failures) == 1
+
+            # Verify batch 0 was scrubbed of docA chunks
+            all_stored = list(store.stream())
+            stored_doc_ids = {c.source_document.id for c in all_stored}
+            assert "docA" not in stored_doc_ids
+            assert "docB" in stored_doc_ids
+
+    @patch(
+        "onyx.indexing.indexing_pipeline.embed_chunks_with_failure_handling",
+    )
+    @patch("onyx.indexing.indexing_pipeline.MAX_CHUNKS_PER_DOC_BATCH", 3)
+    def test_later_batch_skips_already_failed_doc(self, mock_embed: MagicMock) -> None:
+        """If docA fails in batch 0, its chunks in batch 1 are skipped
+        entirely (never sent to the embedder)."""
+        embedded_doc_ids: list[str] = []
+
+        def _embed(
+            chunks: list[DocAwareChunk], **_kwargs: object
+        ) -> tuple[list[IndexChunk], list[ConnectorFailure]]:
+            for c in chunks:
+                embedded_doc_ids.append(c.source_document.id)
+            return _mock_embed_fail_doc("docA")(chunks)
+
+        mock_embed.side_effect = _embed
+
+        with ChunkBatchStore() as store:
+            chunks = [
+                _make_chunk("docA", 0),
+                _make_chunk("docA", 1),
+                _make_chunk("docA", 2),
+                _make_chunk("docA", 3),
+                _make_chunk("docB", 0),
+                _make_chunk("docB", 1),
+            ]
+            _embed_chunks_to_store(
+                chunks=chunks,
+                embedder=MagicMock(),
+                tenant_id="test",
+                request_id=None,
+                store=store,
+            )
+
+        # docA should only appear in batch 0, not batch 1
+        batch_1_doc_ids = embedded_doc_ids[3:]
+        assert "docA" not in batch_1_doc_ids
+
+    @patch(
+        "onyx.indexing.indexing_pipeline.embed_chunks_with_failure_handling",
+    )
+    @patch("onyx.indexing.indexing_pipeline.MAX_CHUNKS_PER_DOC_BATCH", 3)
+    def test_failed_doc_skipped_in_later_batch_while_other_doc_succeeds(
+        self, mock_embed: MagicMock
+    ) -> None:
+        """doc1 spans batches 0 and 1, doc2 only in batch 1.  Batch 0 fails
+        doc1.  In batch 1, doc1 chunks should be skipped but doc2 chunks
+        should still be embedded successfully."""
+        embedded_chunks: list[list[str]] = []
+
+        def _embed(
+            chunks: list[DocAwareChunk], **_kwargs: object
+        ) -> tuple[list[IndexChunk], list[ConnectorFailure]]:
+            embedded_chunks.append([c.source_document.id for c in chunks])
+            return _mock_embed_fail_doc("doc1")(chunks)
+
+        mock_embed.side_effect = _embed
+
+        with ChunkBatchStore() as store:
+            chunks = [
+                _make_chunk("doc1", 0),
+                _make_chunk("doc1", 1),
+                _make_chunk("doc1", 2),
+                _make_chunk("doc1", 3),
+                _make_chunk("doc2", 0),
+                _make_chunk("doc2", 1),
+            ]
+            result = _embed_chunks_to_store(
+                chunks=chunks,
+                embedder=MagicMock(),
+                tenant_id="test",
+                request_id=None,
+                store=store,
+            )
+
+            # doc1 should be fully excluded, doc2 fully included
+            successful_doc_ids = {doc_id for _, doc_id in result.successful_chunk_ids}
+            assert "doc1" not in successful_doc_ids
+            assert "doc2" in successful_doc_ids
+            assert len(result.successful_chunk_ids) == 2  # doc2's 2 chunks
+
+            # Batch 1 should only contain doc2 (doc1 was filtered before embedding)
+            assert len(embedded_chunks) == 2
+            assert "doc1" not in embedded_chunks[1]
+            assert embedded_chunks[1] == ["doc2", "doc2"]
+
+            # Verify on-disk state has no doc1 chunks
+            all_stored = list(store.stream())
+            assert all(c.source_document.id == "doc2" for c in all_stored)
+
+    @patch(
+        "onyx.indexing.indexing_pipeline.embed_chunks_with_failure_handling",
+    )
+    def test_empty_input(self, mock_embed: MagicMock) -> None:
+        """Empty chunk list produces empty results."""
+        mock_embed.side_effect = _mock_embed_success
+
+        with ChunkBatchStore() as store:
+            result = _embed_chunks_to_store(
+                chunks=[],
+                embedder=MagicMock(),
+                tenant_id="test",
+                request_id=None,
+                store=store,
+            )
+
+            assert len(result.successful_chunk_ids) == 0
+            assert len(result.connector_failures) == 0
+            mock_embed.assert_not_called()
+
+    @patch(
+        "onyx.indexing.indexing_pipeline.embed_chunks_with_failure_handling",
+    )
+    @patch("onyx.indexing.indexing_pipeline.MAX_CHUNKS_PER_DOC_BATCH", 100)
+    def test_all_chunks_fail(self, mock_embed: MagicMock) -> None:
+        """When all documents fail, results have no successful chunks."""
+
+        def _fail_all(
+            chunks: list[DocAwareChunk], **_kwargs: object
+        ) -> tuple[list[IndexChunk], list[ConnectorFailure]]:
+            doc_ids = {c.source_document.id for c in chunks}
+            return [], [_make_failure(doc_id) for doc_id in doc_ids]
+
+        mock_embed.side_effect = _fail_all
+
+        with ChunkBatchStore() as store:
+            chunks = [_make_chunk("doc1", 0), _make_chunk("doc2", 1)]
+            result = _embed_chunks_to_store(
+                chunks=chunks,
+                embedder=MagicMock(),
+                tenant_id="test",
+                request_id=None,
+                store=store,
+            )
+
+            assert len(result.successful_chunk_ids) == 0
+            assert len(result.connector_failures) == 2

backend/tests/unit/onyx/indexing/test_personas_in_chunks.py

@@ -116,7 +116,7 @@ def _run_adapter_build(
     project_ids_map: dict[str, list[int]],
     persona_ids_map: dict[str, list[int]],
 ) -> list[DocMetadataAwareIndexChunk]:
-    """Helper that runs UserFileIndexingAdapter.build_metadata_aware_chunks
+    """Helper that runs UserFileIndexingAdapter.prepare_enrichment + enrich_chunk
     with all external dependencies mocked."""
     from onyx.indexing.adapters.user_file_indexing_adapter import (
         UserFileIndexingAdapter,
@@ -155,18 +155,16 @@ def _run_adapter_build(
             side_effect=Exception("no LLM in tests"),
         ),
     ):
-        result = adapter.build_metadata_aware_chunks(
-            chunks_with_embeddings=[chunk],
-            chunk_content_scores=[1.0],
-            tenant_id="test_tenant",
+        enricher = adapter.prepare_enrichment(
             context=context,
+            tenant_id="test_tenant",
+            chunks=[chunk],
         )
-
-    return result.chunks
+        return [enricher.enrich_chunk(chunk, 1.0)]
 
 
-def test_build_metadata_aware_chunks_includes_persona_ids() -> None:
-    """UserFileIndexingAdapter.build_metadata_aware_chunks writes persona IDs
+def test_prepare_enrichment_includes_persona_ids() -> None:
+    """UserFileIndexingAdapter.prepare_enrichment writes persona IDs
     fetched from the DB into each chunk's metadata."""
     file_id = str(uuid4())
     persona_ids = [5, 12]
@@ -183,7 +181,7 @@ def test_build_metadata_aware_chunks_includes_persona_ids() -> None:
     assert chunks[0].user_project == project_ids
 
 
-def test_build_metadata_aware_chunks_missing_file_defaults_to_empty() -> None:
+def test_prepare_enrichment_missing_file_defaults_to_empty() -> None:
     """When a file has no persona or project associations in the DB, the
     adapter should default to empty lists (not KeyError or None)."""
     file_id = str(uuid4())

backend/tests/unit/onyx/llm/test_multi_llm.py

@@ -11,6 +11,7 @@ from litellm.types.utils import ChatCompletionDeltaToolCall
 from litellm.types.utils import Delta
 from litellm.types.utils import Function as LiteLLMFunction
 
+import onyx.llm.models
 from onyx.configs.app_configs import MOCK_LLM_RESPONSE
 from onyx.llm.constants import LlmProviderNames
 from onyx.llm.interfaces import LLMUserIdentity
@@ -1479,6 +1480,147 @@ def test_bifrost_normalizes_api_base_in_model_kwargs() -> None:
     assert llm._model_kwargs["api_base"] == "https://bifrost.example.com/v1"
 
 
+def test_prompt_contains_tool_call_history_true() -> None:
+    from onyx.llm.multi_llm import _prompt_contains_tool_call_history
+
+    messages: LanguageModelInput = [
+        UserMessage(content="What's the weather?"),
+        AssistantMessage(
+            content=None,
+            tool_calls=[
+                ToolCall(
+                    id="tc_1",
+                    function=FunctionCall(name="get_weather", arguments="{}"),
+                )
+            ],
+        ),
+    ]
+    assert _prompt_contains_tool_call_history(messages) is True
+
+
+def test_prompt_contains_tool_call_history_false_no_tools() -> None:
+    from onyx.llm.multi_llm import _prompt_contains_tool_call_history
+
+    messages: LanguageModelInput = [
+        UserMessage(content="Hello"),
+        AssistantMessage(content="Hi there!"),
+    ]
+    assert _prompt_contains_tool_call_history(messages) is False
+
+
+def test_prompt_contains_tool_call_history_false_user_only() -> None:
+    from onyx.llm.multi_llm import _prompt_contains_tool_call_history
+
+    messages: LanguageModelInput = [UserMessage(content="Hello")]
+    assert _prompt_contains_tool_call_history(messages) is False
+
+
+def test_bedrock_claude_drops_thinking_when_thinking_blocks_missing() -> None:
+    """When thinking is enabled but assistant messages with tool_calls lack
+    thinking_blocks, the thinking param must be dropped to avoid the Bedrock
+    BadRequestError about missing thinking blocks."""
+    llm = LitellmLLM(
+        api_key=None,
+        timeout=30,
+        model_provider=LlmProviderNames.BEDROCK,
+        model_name="anthropic.claude-sonnet-4-20250514-v1:0",
+        max_input_tokens=200000,
+    )
+
+    messages: LanguageModelInput = [
+        UserMessage(content="What's the weather?"),
+        AssistantMessage(
+            content=None,
+            tool_calls=[
+                ToolCall(
+                    id="tc_1",
+                    function=FunctionCall(
+                        name="get_weather",
+                        arguments='{"city": "Paris"}',
+                    ),
+                )
+            ],
+        ),
+        onyx.llm.models.ToolMessage(
+            content="22°C sunny",
+            tool_call_id="tc_1",
+        ),
+    ]
+
+    tools = [
+        {
+            "type": "function",
+            "function": {
+                "name": "get_weather",
+                "description": "Get the weather",
+                "parameters": {
+                    "type": "object",
+                    "properties": {"city": {"type": "string"}},
+                },
+            },
+        }
+    ]
+
+    with (
+        patch("litellm.completion") as mock_completion,
+        patch("onyx.llm.multi_llm.model_is_reasoning_model", return_value=True),
+    ):
+        mock_completion.return_value = []
+
+        list(llm.stream(messages, tools=tools, reasoning_effort=ReasoningEffort.HIGH))
+
+        kwargs = mock_completion.call_args.kwargs
+        assert "thinking" not in kwargs, (
+            "thinking param should be dropped when thinking_blocks are missing "
+            "from assistant messages with tool_calls"
+        )
+
+
+def test_bedrock_claude_keeps_thinking_when_no_tool_history() -> None:
+    """When thinking is enabled and there are no historical assistant messages
+    with tool_calls, the thinking param should be preserved."""
+    llm = LitellmLLM(
+        api_key=None,
+        timeout=30,
+        model_provider=LlmProviderNames.BEDROCK,
+        model_name="anthropic.claude-sonnet-4-20250514-v1:0",
+        max_input_tokens=200000,
+    )
+
+    messages: LanguageModelInput = [
+        UserMessage(content="What's the weather?"),
+    ]
+
+    tools = [
+        {
+            "type": "function",
+            "function": {
+                "name": "get_weather",
+                "description": "Get the weather",
+                "parameters": {
+                    "type": "object",
+                    "properties": {"city": {"type": "string"}},
+                },
+            },
+        }
+    ]
+
+    with (
+        patch("litellm.completion") as mock_completion,
+        patch("onyx.llm.multi_llm.model_is_reasoning_model", return_value=True),
+    ):
+        mock_completion.return_value = []
+
+        list(llm.stream(messages, tools=tools, reasoning_effort=ReasoningEffort.HIGH))
+
+        kwargs = mock_completion.call_args.kwargs
+        assert "thinking" in kwargs, (
+            "thinking param should be preserved when no assistant messages "
+            "with tool_calls exist in history"
+        )
+        assert kwargs["thinking"]["type"] == "enabled"
+
+
 def test_bifrost_claude_includes_allowed_openai_params() -> None:
     llm = LitellmLLM(
         api_key="test_key",

cli/README.md

@@ -63,6 +63,31 @@ onyx-cli agents
 onyx-cli agents --json
 ```
 
+### Serve over SSH
+
+```shell
+# Start a public SSH endpoint for the CLI TUI
+onyx-cli serve --host 0.0.0.0 --port 2222
+
+# Connect as a client
+ssh your-host -p 2222
+```
+
+Clients can either:
+- paste an API key at the login prompt, or
+- skip the prompt by sending `ONYX_API_KEY` over SSH:
+
+```shell
+export ONYX_API_KEY=your-key
+ssh -o SendEnv=ONYX_API_KEY your-host -p 2222
+```
+
+Useful hardening flags:
+- `--idle-timeout` (default `15m`)
+- `--max-session-timeout` (default `8h`)
+- `--rate-limit-per-minute` (default `20`)
+- `--rate-limit-burst` (default `40`)
+
 ## Commands
 
 | Command | Description |
@@ -70,6 +95,7 @@ onyx-cli agents --json
 | `chat` | Launch the interactive chat TUI (default) |
 | `ask` | Ask a one-shot question (non-interactive) |
 | `agents` | List available agents |
+| `serve` | Serve the interactive chat TUI over SSH |
 | `configure` | Configure server URL and API key |
 | `validate-config` | Validate configuration and test connection |
 

cli/cmd/root.go

@@ -96,6 +96,7 @@ func Execute() error {
 	rootCmd.AddCommand(newAgentsCmd())
 	rootCmd.AddCommand(newConfigureCmd())
 	rootCmd.AddCommand(newValidateConfigCmd())
+	rootCmd.AddCommand(newServeCmd())
 
 	// Default command is chat, but intercept --version first
 	rootCmd.RunE = func(cmd *cobra.Command, args []string) error {

cli/cmd/serve.go

@@ -0,0 +1,450 @@
+package cmd
+
+import (
+	"context"
+	"errors"
+	"fmt"
+	"net"
+	"os"
+	"os/signal"
+	"path/filepath"
+	"strings"
+	"syscall"
+	"time"
+
+	"github.com/charmbracelet/bubbles/textinput"
+	tea "github.com/charmbracelet/bubbletea"
+	"github.com/charmbracelet/log"
+	"github.com/charmbracelet/ssh"
+	"github.com/charmbracelet/wish"
+	"github.com/charmbracelet/wish/activeterm"
+	"github.com/charmbracelet/wish/bubbletea"
+	"github.com/charmbracelet/wish/logging"
+	"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/tui"
+	"github.com/spf13/cobra"
+	"golang.org/x/time/rate"
+)
+
+const (
+	defaultServeIdleTimeout        = 15 * time.Minute
+	defaultServeMaxSessionTimeout  = 8 * time.Hour
+	defaultServeRateLimitPerMinute = 20
+	defaultServeRateLimitBurst     = 40
+	defaultServeRateLimitCacheSize = 4096
+	maxAPIKeyLength                = 512
+	apiKeyValidationTimeout        = 15 * time.Second
+	maxAPIKeyRetries               = 5
+)
+
+func sessionEnv(s ssh.Session, key string) string {
+	prefix := key + "="
+	for _, env := range s.Environ() {
+		if strings.HasPrefix(env, prefix) {
+			return env[len(prefix):]
+		}
+	}
+	return ""
+}
+
+func validateAPIKey(serverURL string, apiKey string) error {
+	trimmedKey := strings.TrimSpace(apiKey)
+	if len(trimmedKey) > maxAPIKeyLength {
+		return fmt.Errorf("API key is too long (max %d characters)", maxAPIKeyLength)
+	}
+
+	cfg := config.OnyxCliConfig{
+		ServerURL: serverURL,
+		APIKey:    trimmedKey,
+	}
+	client := api.NewClient(cfg)
+	ctx, cancel := context.WithTimeout(context.Background(), apiKeyValidationTimeout)
+	defer cancel()
+	return client.TestConnection(ctx)
+}
+
+// --- auth prompt (bubbletea model) ---
+
+type authState int
+
+const (
+	authInput authState = iota
+	authValidating
+	authDone
+)
+
+type authValidatedMsg struct {
+	key string
+	err error
+}
+
+type authModel struct {
+	input     textinput.Model
+	serverURL string
+	state     authState
+	apiKey    string // set on successful validation
+	errMsg    string
+	retries   int
+	aborted   bool
+}
+
+func newAuthModel(serverURL, initialErr string) authModel {
+	ti := textinput.New()
+	ti.Prompt = "  API Key: "
+	ti.EchoMode = textinput.EchoPassword
+	ti.EchoCharacter = '•'
+	ti.CharLimit = maxAPIKeyLength
+	ti.Width = 80
+	ti.Focus()
+
+	return authModel{
+		input:     ti,
+		serverURL: serverURL,
+		errMsg:    initialErr,
+	}
+}
+
+func (m authModel) Update(msg tea.Msg) (authModel, tea.Cmd) {
+	switch msg := msg.(type) {
+	case tea.WindowSizeMsg:
+		m.input.Width = max(msg.Width-14, 20) // account for prompt width
+		return m, nil
+	case tea.KeyMsg:
+		switch msg.Type {
+		case tea.KeyCtrlC, tea.KeyCtrlD:
+			m.aborted = true
+			return m, nil
+		default:
+			if m.state == authValidating {
+				return m, nil
+			}
+		}
+		switch msg.Type {
+		case tea.KeyEnter:
+			key := strings.TrimSpace(m.input.Value())
+			if key == "" {
+				m.errMsg = "No key entered."
+				m.retries++
+				if m.retries >= maxAPIKeyRetries {
+					m.errMsg = "Too many failed attempts. Disconnecting."
+					m.aborted = true
+					return m, nil
+				}
+				m.input.SetValue("")
+				return m, nil
+			}
+			m.state = authValidating
+			m.errMsg = ""
+			serverURL := m.serverURL
+			return m, func() tea.Msg {
+				return authValidatedMsg{key: key, err: validateAPIKey(serverURL, key)}
+			}
+		}
+
+	case authValidatedMsg:
+		if msg.err != nil {
+			m.state = authInput
+			m.errMsg = msg.err.Error()
+			m.retries++
+			if m.retries >= maxAPIKeyRetries {
+				m.errMsg = "Too many failed attempts. Disconnecting."
+				m.aborted = true
+				return m, nil
+			}
+			m.input.SetValue("")
+			return m, m.input.Focus()
+		}
+		m.apiKey = msg.key
+		m.state = authDone
+		return m, nil
+	}
+
+	if m.state == authInput {
+		var cmd tea.Cmd
+		m.input, cmd = m.input.Update(msg)
+		return m, cmd
+	}
+	return m, nil
+}
+
+func (m authModel) View() string {
+	settingsURL := strings.TrimRight(m.serverURL, "/") + "/app/settings/accounts-access"
+
+	var b strings.Builder
+	b.WriteString("\n")
+	b.WriteString("  \x1b[1;35mOnyx CLI\x1b[0m\n")
+	b.WriteString("  \x1b[90m" + m.serverURL + "\x1b[0m\n")
+	b.WriteString("\n")
+	b.WriteString("  Generate an API key at:\n")
+	b.WriteString("  \x1b[4;34m" + settingsURL + "\x1b[0m\n")
+	b.WriteString("\n")
+	b.WriteString("  \x1b[90mTip: skip this prompt by passing your key via SSH:\x1b[0m\n")
+	b.WriteString("  \x1b[90m  export ONYX_API_KEY=<key>\x1b[0m\n")
+	b.WriteString("  \x1b[90m  ssh -o SendEnv=ONYX_API_KEY <host> -p <port>\x1b[0m\n")
+	b.WriteString("\n")
+
+	if m.errMsg != "" {
+		b.WriteString("  \x1b[1;31m" + m.errMsg + "\x1b[0m\n\n")
+	}
+
+	switch m.state {
+	case authDone:
+		b.WriteString("  \x1b[32mAuthenticated.\x1b[0m\n")
+	case authValidating:
+		b.WriteString("  \x1b[90mValidating…\x1b[0m\n")
+	default:
+		b.WriteString(m.input.View() + "\n")
+	}
+
+	return b.String()
+}
+
+// --- serve model (wraps auth → TUI in a single bubbletea program) ---
+
+type serveModel struct {
+	auth      authModel
+	tui       tea.Model
+	authed    bool
+	serverCfg config.OnyxCliConfig
+	width     int
+	height    int
+}
+
+func newServeModel(serverCfg config.OnyxCliConfig, initialErr string) serveModel {
+	return serveModel{
+		auth:      newAuthModel(serverCfg.ServerURL, initialErr),
+		serverCfg: serverCfg,
+	}
+}
+
+func (m serveModel) Init() tea.Cmd {
+	return textinput.Blink
+}
+
+func (m serveModel) Update(msg tea.Msg) (tea.Model, tea.Cmd) {
+	if !m.authed {
+		if ws, ok := msg.(tea.WindowSizeMsg); ok {
+			m.width = ws.Width
+			m.height = ws.Height
+		}
+
+		var cmd tea.Cmd
+		m.auth, cmd = m.auth.Update(msg)
+
+		if m.auth.aborted {
+			return m, tea.Quit
+		}
+		if m.auth.apiKey != "" {
+			cfg := config.OnyxCliConfig{
+				ServerURL:      m.serverCfg.ServerURL,
+				APIKey:         m.auth.apiKey,
+				DefaultAgentID: m.serverCfg.DefaultAgentID,
+			}
+			m.tui = tui.NewModel(cfg)
+			m.authed = true
+			w, h := m.width, m.height
+			return m, tea.Batch(
+				tea.EnterAltScreen,
+				tea.EnableMouseCellMotion,
+				m.tui.Init(),
+				func() tea.Msg { return tea.WindowSizeMsg{Width: w, Height: h} },
+			)
+		}
+		return m, cmd
+	}
+
+	var cmd tea.Cmd
+	m.tui, cmd = m.tui.Update(msg)
+	return m, cmd
+}
+
+func (m serveModel) View() string {
+	if !m.authed {
+		return m.auth.View()
+	}
+	return m.tui.View()
+}
+
+// --- serve command ---
+
+func newServeCmd() *cobra.Command {
+	var (
+		host              string
+		port              int
+		keyPath           string
+		idleTimeout       time.Duration
+		maxSessionTimeout time.Duration
+		rateLimitPerMin   int
+		rateLimitBurst    int
+		rateLimitCache    int
+	)
+
+	cmd := &cobra.Command{
+		Use:   "serve",
+		Short: "Serve the Onyx TUI over SSH",
+		Long: `Start an SSH server that presents the interactive Onyx chat TUI to
+connecting clients. Each SSH session gets its own independent TUI instance.
+
+Clients are prompted for their Onyx API key on connect. The key can also be
+provided via the ONYX_API_KEY environment variable to skip the prompt:
+
+  ssh -o SendEnv=ONYX_API_KEY host -p port
+
+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`,
+		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")
+			}
+			if !cmd.Flags().Changed("host-key") {
+				if v := os.Getenv(config.EnvSSHHostKey); v != "" {
+					keyPath = v
+				}
+			}
+			if rateLimitPerMin <= 0 {
+				return fmt.Errorf("--rate-limit-per-minute must be > 0")
+			}
+			if rateLimitBurst <= 0 {
+				return fmt.Errorf("--rate-limit-burst must be > 0")
+			}
+			if rateLimitCache <= 0 {
+				return fmt.Errorf("--rate-limit-cache must be > 0")
+			}
+
+			addr := net.JoinHostPort(host, fmt.Sprintf("%d", port))
+			connectionLimiter := ratelimiter.NewRateLimiter(
+				rate.Limit(float64(rateLimitPerMin)/60.0),
+				rateLimitBurst,
+				rateLimitCache,
+			)
+
+			handler := func(s ssh.Session) (tea.Model, []tea.ProgramOption) {
+				apiKey := strings.TrimSpace(sessionEnv(s, config.EnvAPIKey))
+				var envErr string
+
+				if apiKey != "" {
+					if err := validateAPIKey(serverCfg.ServerURL, apiKey); err != nil {
+						envErr = fmt.Sprintf("ONYX_API_KEY from SSH environment is invalid: %s", err.Error())
+						apiKey = ""
+					}
+				}
+
+				if apiKey != "" {
+					// Env key is valid — go straight to the TUI.
+					cfg := config.OnyxCliConfig{
+						ServerURL:      serverCfg.ServerURL,
+						APIKey:         apiKey,
+						DefaultAgentID: serverCfg.DefaultAgentID,
+					}
+					return tui.NewModel(cfg), []tea.ProgramOption{
+						tea.WithAltScreen(),
+						tea.WithMouseCellMotion(),
+					}
+				}
+
+				// No valid env key — show auth prompt, then transition
+				// to the TUI within the same bubbletea program.
+				return newServeModel(serverCfg, envErr), []tea.ProgramOption{
+					tea.WithMouseCellMotion(),
+				}
+			}
+
+			serverOptions := []ssh.Option{
+				wish.WithAddress(addr),
+				wish.WithHostKeyPath(keyPath),
+				wish.WithMiddleware(
+					bubbletea.Middleware(handler),
+					activeterm.Middleware(),
+					ratelimiter.Middleware(connectionLimiter),
+					logging.Middleware(),
+				),
+			}
+			if idleTimeout > 0 {
+				serverOptions = append(serverOptions, wish.WithIdleTimeout(idleTimeout))
+			}
+			if maxSessionTimeout > 0 {
+				serverOptions = append(serverOptions, wish.WithMaxTimeout(maxSessionTimeout))
+			}
+
+			s, err := wish.NewServer(serverOptions...)
+			if err != nil {
+				return fmt.Errorf("could not create SSH server: %w", err)
+			}
+
+			done := make(chan os.Signal, 1)
+			signal.Notify(done, os.Interrupt, syscall.SIGTERM)
+
+			log.Info("Starting Onyx SSH server", "addr", addr)
+			log.Info("Connect with", "cmd", fmt.Sprintf("ssh %s -p %d", host, port))
+
+			errCh := make(chan error, 1)
+			go func() {
+				if err := s.ListenAndServe(); err != nil && !errors.Is(err, ssh.ErrServerClosed) {
+					log.Error("SSH server failed", "error", err)
+					errCh <- err
+				}
+			}()
+
+			var serverErr error
+			select {
+			case <-done:
+			case serverErr = <-errCh:
+			}
+
+			signal.Stop(done)
+			log.Info("Shutting down SSH server")
+			ctx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
+			defer cancel()
+			if shutdownErr := s.Shutdown(ctx); shutdownErr != nil {
+				return errors.Join(serverErr, shutdownErr)
+			}
+			return serverErr
+		},
+	}
+
+	cmd.Flags().StringVar(&host, "host", "localhost", "Host address to bind to")
+	cmd.Flags().IntVarP(&port, "port", "p", 2222, "Port to listen on")
+	cmd.Flags().StringVar(&keyPath, "host-key", filepath.Join(config.ConfigDir(), "host_ed25519"),
+		"Path to SSH host key (auto-generated if missing)")
+	cmd.Flags().DurationVar(
+		&idleTimeout,
+		"idle-timeout",
+		defaultServeIdleTimeout,
+		"Disconnect idle clients after this duration (set 0 to disable)",
+	)
+	cmd.Flags().DurationVar(
+		&maxSessionTimeout,
+		"max-session-timeout",
+		defaultServeMaxSessionTimeout,
+		"Maximum lifetime of a client session (set 0 to disable)",
+	)
+	cmd.Flags().IntVar(
+		&rateLimitPerMin,
+		"rate-limit-per-minute",
+		defaultServeRateLimitPerMinute,
+		"Per-IP connection rate limit (new sessions per minute)",
+	)
+	cmd.Flags().IntVar(
+		&rateLimitBurst,
+		"rate-limit-burst",
+		defaultServeRateLimitBurst,
+		"Per-IP burst limit for connection attempts",
+	)
+	cmd.Flags().IntVar(
+		&rateLimitCache,
+		"rate-limit-cache",
+		defaultServeRateLimitCacheSize,
+		"Maximum number of IP limiter entries tracked in memory",
+	)
+
+	return cmd
+}

cli/go.mod

@@ -7,27 +7,40 @@ require (
 	github.com/charmbracelet/bubbletea v1.3.10
 	github.com/charmbracelet/glamour v1.0.0
 	github.com/charmbracelet/lipgloss v1.1.1-0.20250404203927-76690c660834
+	github.com/charmbracelet/log v1.0.0
+	github.com/charmbracelet/ssh v0.0.0-20250826160808-ebfa259c7309
+	github.com/charmbracelet/wish v1.4.7
 	github.com/sirupsen/logrus v1.9.4
 	github.com/spf13/cobra v1.10.2
 	golang.org/x/term v0.41.0
 	golang.org/x/text v0.35.0
+	golang.org/x/time v0.15.0
 )
 
 require (
 	github.com/alecthomas/chroma/v2 v2.23.1 // indirect
+	github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be // indirect
 	github.com/atotto/clipboard v0.1.4 // indirect
 	github.com/aymanbagabas/go-osc52/v2 v2.0.1 // indirect
 	github.com/aymerick/douceur v0.2.0 // indirect
 	github.com/charmbracelet/colorprofile v0.4.3 // indirect
+	github.com/charmbracelet/keygen v0.5.4 // indirect
 	github.com/charmbracelet/x/ansi v0.11.6 // indirect
 	github.com/charmbracelet/x/cellbuf v0.0.15 // indirect
+	github.com/charmbracelet/x/conpty v0.2.0 // indirect
 	github.com/charmbracelet/x/exp/slice v0.0.0-20260323091123-df7b1bcffcca // indirect
+	github.com/charmbracelet/x/input v0.3.7 // indirect
 	github.com/charmbracelet/x/term v0.2.2 // indirect
+	github.com/charmbracelet/x/termios v0.1.1 // indirect
+	github.com/charmbracelet/x/windows v0.2.2 // indirect
 	github.com/clipperhouse/displaywidth v0.11.0 // indirect
 	github.com/clipperhouse/uax29/v2 v2.7.0 // indirect
+	github.com/creack/pty v1.1.24 // indirect
 	github.com/dlclark/regexp2 v1.11.5 // indirect
 	github.com/erikgeiser/coninput v0.0.0-20211004153227-1c3628e74d0f // indirect
+	github.com/go-logfmt/logfmt v0.6.1 // indirect
 	github.com/gorilla/css v1.0.1 // indirect
+	github.com/hashicorp/golang-lru/v2 v2.0.7 // indirect
 	github.com/inconshreveable/mousetrap v1.1.0 // indirect
 	github.com/lucasb-eyer/go-colorful v1.3.0 // indirect
 	github.com/mattn/go-isatty v0.0.20 // indirect
@@ -43,6 +56,8 @@ require (
 	github.com/xo/terminfo v0.0.0-20220910002029-abceb7e1c41e // indirect
 	github.com/yuin/goldmark v1.8.2 // indirect
 	github.com/yuin/goldmark-emoji v1.0.6 // indirect
+	golang.org/x/crypto v0.49.0 // indirect
+	golang.org/x/exp v0.0.0-20260312153236-7ab1446f8b90 // indirect
 	golang.org/x/net v0.52.0 // indirect
 	golang.org/x/sys v0.42.0 // indirect
 )

cli/go.sum

@@ -4,6 +4,8 @@ github.com/alecthomas/chroma/v2 v2.23.1 h1:nv2AVZdTyClGbVQkIzlDm/rnhk1E9bU9nXwmZ
 github.com/alecthomas/chroma/v2 v2.23.1/go.mod h1:NqVhfBR0lte5Ouh3DcthuUCTUpDC9cxBOfyMbMQPs3o=
 github.com/alecthomas/repr v0.5.2 h1:SU73FTI9D1P5UNtvseffFSGmdNci/O6RsqzeXJtP0Qs=
 github.com/alecthomas/repr v0.5.2/go.mod h1:Fr0507jx4eOXV7AlPV6AVZLYrLIuIeSOWtW57eE/O/4=
+github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be h1:9AeTilPcZAjCFIImctFaOjnTIavg87rW78vTPkQqLI8=
+github.com/anmitsu/go-shlex v0.0.0-20200514113438-38f4b401e2be/go.mod h1:ySMOLuWl6zY27l47sB3qLNK6tF2fkHG55UZxx8oIVo4=
 github.com/atotto/clipboard v0.1.4 h1:EH0zSVneZPSuFR11BlR9YppQTVDbh5+16AmcJi4g1z4=
 github.com/atotto/clipboard v0.1.4/go.mod h1:ZY9tmq7sm5xIbd9bOK4onWV4S6X0u6GY7Vn0Yu86PYI=
 github.com/aymanbagabas/go-osc52/v2 v2.0.1 h1:HwpRHbFMcZLEVr42D4p7XBqjyuxQH5SMiErDT4WkJ2k=
@@ -20,31 +22,55 @@ github.com/charmbracelet/colorprofile v0.4.3 h1:QPa1IWkYI+AOB+fE+mg/5/4HRMZcaXex
 github.com/charmbracelet/colorprofile v0.4.3/go.mod h1:/zT4BhpD5aGFpqQQqw7a+VtHCzu+zrQtt1zhMt9mR4Q=
 github.com/charmbracelet/glamour v1.0.0 h1:AWMLOVFHTsysl4WV8T8QgkQ0s/ZNZo7CiE4WKhk8l08=
 github.com/charmbracelet/glamour v1.0.0/go.mod h1:DSdohgOBkMr2ZQNhw4LZxSGpx3SvpeujNoXrQyH2hxo=
+github.com/charmbracelet/keygen v0.5.4 h1:XQYgf6UEaTGgQSSmiPpIQ78WfseNQp4Pz8N/c1OsrdA=
+github.com/charmbracelet/keygen v0.5.4/go.mod h1:t4oBRr41bvK7FaJsAaAQhhkUuHslzFXVjOBwA55CZNM=
 github.com/charmbracelet/lipgloss v1.1.1-0.20250404203927-76690c660834 h1:ZR7e0ro+SZZiIZD7msJyA+NjkCNNavuiPBLgerbOziE=
 github.com/charmbracelet/lipgloss v1.1.1-0.20250404203927-76690c660834/go.mod h1:aKC/t2arECF6rNOnaKaVU6y4t4ZeHQzqfxedE/VkVhA=
+github.com/charmbracelet/log v1.0.0 h1:HVVVMmfOorfj3BA9i8X8UL69Hoz9lI0PYwXfJvOdRc4=
+github.com/charmbracelet/log v1.0.0/go.mod h1:uYgY3SmLpwJWxmlrPwXvzVYujxis1vAKRV/0VQB7yWA=
+github.com/charmbracelet/ssh v0.0.0-20250826160808-ebfa259c7309 h1:dCVbCRRtg9+tsfiTXTp0WupDlHruAXyp+YoxGVofHHc=
+github.com/charmbracelet/ssh v0.0.0-20250826160808-ebfa259c7309/go.mod h1:R9cISUs5kAH4Cq/rguNbSwcR+slE5Dfm8FEs//uoIGE=
+github.com/charmbracelet/wish v1.4.7 h1:O+jdLac3s6GaqkOHHSwezejNK04vl6VjO1A+hl8J8Yc=
+github.com/charmbracelet/wish v1.4.7/go.mod h1:OBZ8vC62JC5cvbxJLh+bIWtG7Ctmct+ewziuUWK+G14=
 github.com/charmbracelet/x/ansi v0.11.6 h1:GhV21SiDz/45W9AnV2R61xZMRri5NlLnl6CVF7ihZW8=
 github.com/charmbracelet/x/ansi v0.11.6/go.mod h1:2JNYLgQUsyqaiLovhU2Rv/pb8r6ydXKS3NIttu3VGZQ=
 github.com/charmbracelet/x/cellbuf v0.0.15 h1:ur3pZy0o6z/R7EylET877CBxaiE1Sp1GMxoFPAIztPI=
 github.com/charmbracelet/x/cellbuf v0.0.15/go.mod h1:J1YVbR7MUuEGIFPCaaZ96KDl5NoS0DAWkskup+mOY+Q=
+github.com/charmbracelet/x/conpty v0.2.0 h1:eKtA2hm34qNfgJCDp/M6Dc0gLy7e07YEK4qAdNGOvVY=
+github.com/charmbracelet/x/conpty v0.2.0/go.mod h1:fexgUnVrZgw8scD49f6VSi0Ggj9GWYIrpedRthAwW/8=
 github.com/charmbracelet/x/exp/golden v0.0.0-20241011142426-46044092ad91 h1:payRxjMjKgx2PaCWLZ4p3ro9y97+TVLZNaRZgJwSVDQ=
 github.com/charmbracelet/x/exp/golden v0.0.0-20241011142426-46044092ad91/go.mod h1:wDlXFlCrmJ8J+swcL/MnGUuYnqgQdW9rhSD61oNMb6U=
 github.com/charmbracelet/x/exp/slice v0.0.0-20260323091123-df7b1bcffcca h1:QQoyQLgUzojMNWHVHToN6d9qTvT0KWtxUKIRPx/Ox5o=
 github.com/charmbracelet/x/exp/slice v0.0.0-20260323091123-df7b1bcffcca/go.mod h1:vqEfX6xzqW1pKKZUUiFOKg0OQ7bCh54Q2vR/tserrRA=
+github.com/charmbracelet/x/input v0.3.7 h1:UzVbkt1vgM9dBQ+K+uRolBlN6IF2oLchmPKKo/aucXo=
+github.com/charmbracelet/x/input v0.3.7/go.mod h1:ZSS9Cia6Cycf2T6ToKIOxeTBTDwl25AGwArJuGaOBH8=
 github.com/charmbracelet/x/term v0.2.2 h1:xVRT/S2ZcKdhhOuSP4t5cLi5o+JxklsoEObBSgfgZRk=
 github.com/charmbracelet/x/term v0.2.2/go.mod h1:kF8CY5RddLWrsgVwpw4kAa6TESp6EB5y3uxGLeCqzAI=
+github.com/charmbracelet/x/termios v0.1.1 h1:o3Q2bT8eqzGnGPOYheoYS8eEleT5ZVNYNy8JawjaNZY=
+github.com/charmbracelet/x/termios v0.1.1/go.mod h1:rB7fnv1TgOPOyyKRJ9o+AsTU/vK5WHJ2ivHeut/Pcwo=
+github.com/charmbracelet/x/windows v0.2.2 h1:IofanmuvaxnKHuV04sC0eBy/smG6kIKrWG2/jYn2GuM=
+github.com/charmbracelet/x/windows v0.2.2/go.mod h1:/8XtdKZzedat74NQFn0NGlGL4soHB0YQZrETF96h75k=
 github.com/clipperhouse/displaywidth v0.11.0 h1:lBc6kY44VFw+TDx4I8opi/EtL9m20WSEFgwIwO+UVM8=
 github.com/clipperhouse/displaywidth v0.11.0/go.mod h1:bkrFNkf81G8HyVqmKGxsPufD3JhNl3dSqnGhOoSD/o0=
 github.com/clipperhouse/uax29/v2 v2.7.0 h1:+gs4oBZ2gPfVrKPthwbMzWZDaAFPGYK72F0NJv2v7Vk=
 github.com/clipperhouse/uax29/v2 v2.7.0/go.mod h1:EFJ2TJMRUaplDxHKj1qAEhCtQPW2tJSwu5BF98AuoVM=
 github.com/cpuguy83/go-md2man/v2 v2.0.6/go.mod h1:oOW0eioCTA6cOiMLiUPZOpcVxMig6NIQQ7OS05n1F4g=
+github.com/creack/pty v1.1.24 h1:bJrF4RRfyJnbTJqzRLHzcGaZK1NeM5kTC9jGgovnR1s=
+github.com/creack/pty v1.1.24/go.mod h1:08sCNb52WyoAwi2QDyzUCTgcvVFhUzewun7wtTfvcwE=
 github.com/davecgh/go-spew v1.1.1 h1:vj9j/u1bqnvCEfJOwUhtlOARqs3+rkHYY13jYWTU97c=
 github.com/davecgh/go-spew v1.1.1/go.mod h1:J7Y8YcW2NihsgmVo/mv3lAwl/skON4iLHjSsI+c5H38=
 github.com/dlclark/regexp2 v1.11.5 h1:Q/sSnsKerHeCkc/jSTNq1oCm7KiVgUMZRDUoRu0JQZQ=
 github.com/dlclark/regexp2 v1.11.5/go.mod h1:DHkYz0B9wPfa6wondMfaivmHpzrQ3v9q8cnmRbL6yW8=
 github.com/erikgeiser/coninput v0.0.0-20211004153227-1c3628e74d0f h1:Y/CXytFA4m6baUTXGLOoWe4PQhGxaX0KpnayAqC48p4=
 github.com/erikgeiser/coninput v0.0.0-20211004153227-1c3628e74d0f/go.mod h1:vw97MGsxSvLiUE2X8qFplwetxpGLQrlU1Q9AUEIzCaM=
+github.com/go-logfmt/logfmt v0.6.1 h1:4hvbpePJKnIzH1B+8OR/JPbTx37NktoI9LE2QZBBkvE=
+github.com/go-logfmt/logfmt v0.6.1/go.mod h1:EV2pOAQoZaT1ZXZbqDl5hrymndi4SY9ED9/z6CO0XAk=
+github.com/google/go-cmp v0.7.0 h1:wk8382ETsv4JYUZwIsn6YpYiWiBsYLSJiTsyBybVuN8=
+github.com/google/go-cmp v0.7.0/go.mod h1:pXiqmnSA92OHEEa9HXL2W4E7lf9JzCmGVUdgjX3N/iU=
 github.com/gorilla/css v1.0.1 h1:ntNaBIghp6JmvWnxbZKANoLyuXTPZ4cAMlo6RyhlbO8=
 github.com/gorilla/css v1.0.1/go.mod h1:BvnYkspnSzMmwRK+b8/xgNPLiIuNZr6vbZBTPQ2A3b0=
+github.com/hashicorp/golang-lru/v2 v2.0.7 h1:a+bsQ5rvGLjzHuww6tVxozPZFVghXaHOwFs4luLUK2k=
+github.com/hashicorp/golang-lru/v2 v2.0.7/go.mod h1:QeFd9opnmA6QUJc5vARoKUSoFhyfM2/ZepoAG6RGpeM=
 github.com/hexops/gotextdiff v1.0.3 h1:gitA9+qJrrTCsiCl7+kh75nPqQt1cx4ZkudSTLoUqJM=
 github.com/hexops/gotextdiff v1.0.3/go.mod h1:pSWU5MAI3yDq+fZBTazCSJysOMbxWL1BSow5/V2vxeg=
 github.com/inconshreveable/mousetrap v1.1.0 h1:wN+x4NVGpMsO7ErUn/mUI3vEoE6Jt13X2s0bqwp9tc8=
@@ -82,8 +108,8 @@ github.com/spf13/cobra v1.10.2/go.mod h1:7C1pvHqHw5A4vrJfjNwvOdzYu0Gml16OCs2GRiT
 github.com/spf13/pflag v1.0.9/go.mod h1:McXfInJRrz4CZXVZOBLb0bTZqETkiAhM9Iw0y3An2Bg=
 github.com/spf13/pflag v1.0.10 h1:4EBh2KAYBwaONj6b2Ye1GiHfwjqyROoF4RwYO+vPwFk=
 github.com/spf13/pflag v1.0.10/go.mod h1:McXfInJRrz4CZXVZOBLb0bTZqETkiAhM9Iw0y3An2Bg=
-github.com/stretchr/testify v1.10.0 h1:Xv5erBjTwe/5IxqUQTdXv5kgmIvbHo3QQyRwhJsOfJA=
-github.com/stretchr/testify v1.10.0/go.mod h1:r2ic/lqez/lEtzL7wO/rwa5dbSLXVDPFyf8C91i36aY=
+github.com/stretchr/testify v1.11.1 h1:7s2iGBzp5EwR7/aIZr8ao5+dra3wiQyKjjFuvgVKu7U=
+github.com/stretchr/testify v1.11.1/go.mod h1:wZwfW3scLgRK+23gO65QZefKpKQRnfz6sD981Nm4B6U=
 github.com/xo/terminfo v0.0.0-20220910002029-abceb7e1c41e h1:JVG44RsyaB9T2KIHavMF/ppJZNG9ZpyihvCd0w101no=
 github.com/xo/terminfo v0.0.0-20220910002029-abceb7e1c41e/go.mod h1:RbqR21r5mrJuqunuUZ/Dhy/avygyECGrLceyNeo4LiM=
 github.com/yuin/goldmark v1.8.2 h1:kEGpgqJXdgbkhcOgBxkC0X0PmoPG1ZyoZ117rDVp4zE=
@@ -91,10 +117,14 @@ github.com/yuin/goldmark v1.8.2/go.mod h1:ip/1k0VRfGynBgxOz0yCqHrbZXhcjxyuS66Brc
 github.com/yuin/goldmark-emoji v1.0.6 h1:QWfF2FYaXwL74tfGOW5izeiZepUDroDJfWubQI9HTHs=
 github.com/yuin/goldmark-emoji v1.0.6/go.mod h1:ukxJDKFpdFb5x0a5HqbdlcKtebh086iJpI31LTKmWuA=
 go.yaml.in/yaml/v3 v3.0.4/go.mod h1:DhzuOOF2ATzADvBadXxruRBLzYTpT36CKvDb3+aBEFg=
-golang.org/x/exp v0.0.0-20231006140011-7918f672742d h1:jtJma62tbqLibJ5sFQz8bKtEM8rJBtfilJ2qTU199MI=
-golang.org/x/exp v0.0.0-20231006140011-7918f672742d/go.mod h1:ldy0pHrwJyGW56pPQzzkH36rKxoZW1tw7ZJpeKx+hdo=
+golang.org/x/crypto v0.49.0 h1:+Ng2ULVvLHnJ/ZFEq4KdcDd/cfjrrjjNSXNzxg0Y4U4=
+golang.org/x/crypto v0.49.0/go.mod h1:ErX4dUh2UM+CFYiXZRTcMpEcN8b/1gxEuv3nODoYtCA=
+golang.org/x/exp v0.0.0-20260312153236-7ab1446f8b90 h1:jiDhWWeC7jfWqR9c/uplMOqJ0sbNlNWv0UkzE0vX1MA=
+golang.org/x/exp v0.0.0-20260312153236-7ab1446f8b90/go.mod h1:xE1HEv6b+1SCZ5/uscMRjUBKtIxworgEcEi+/n9NQDQ=
 golang.org/x/net v0.52.0 h1:He/TN1l0e4mmR3QqHMT2Xab3Aj3L9qjbhRm78/6jrW0=
 golang.org/x/net v0.52.0/go.mod h1:R1MAz7uMZxVMualyPXb+VaqGSa3LIaUqk0eEt3w36Sw=
+golang.org/x/sync v0.20.0 h1:e0PTpb7pjO8GAtTs2dQ6jYa5BWYlMuX047Dco/pItO4=
+golang.org/x/sync v0.20.0/go.mod h1:9xrNwdLfx4jkKbNva9FpL6vEN7evnE43NNNJQ2LF3+0=
 golang.org/x/sys v0.0.0-20210809222454-d867a43fc93e/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.6.0/go.mod h1:oPkhp1MJrh7nUepCBck5+mAzfO9JrbApNNgaTdGDITg=
 golang.org/x/sys v0.42.0 h1:omrd2nAlyT5ESRdCLYdm3+fMfNFE/+Rf4bDIQImRJeo=
@@ -103,6 +133,8 @@ golang.org/x/term v0.41.0 h1:QCgPso/Q3RTJx2Th4bDLqML4W6iJiaXFq2/ftQF13YU=
 golang.org/x/term v0.41.0/go.mod h1:3pfBgksrReYfZ5lvYM0kSO0LIkAl4Yl2bXOkKP7Ec2A=
 golang.org/x/text v0.35.0 h1:JOVx6vVDFokkpaq1AEptVzLTpDe9KGpj5tR4/X+ybL8=
 golang.org/x/text v0.35.0/go.mod h1:khi/HExzZJ2pGnjenulevKNX1W67CUy0AsXcNubPGCA=
+golang.org/x/time v0.15.0 h1:bbrp8t3bGUeFOx08pvsMYRTCVSMk89u4tKbNOZbp88U=
+golang.org/x/time v0.15.0/go.mod h1:Y4YMaQmXwGQZoFaVFk4YpCt4FLQMYKZe9oeV/f4MSno=
 gopkg.in/check.v1 v0.0.0-20161208181325-20d25e280405/go.mod h1:Co6ibVJAznAaIkqp8huTwlJQCZ016jof/cbN4VW5Yz0=
 gopkg.in/yaml.v3 v3.0.1 h1:fxVm/GzAzEWqLHuvctI91KS9hhNmmWOoWu0XTYJS7CA=
 gopkg.in/yaml.v3 v3.0.1/go.mod h1:K4uyk7z7BCEPqu6E+C64Yfv1cQ7kz7rIZviUmN+EgEM=

cli/internal/config/config.go

@@ -9,9 +9,10 @@ import (
 )
 
 const (
-	EnvServerURL    = "ONYX_SERVER_URL"
-	EnvAPIKey = "ONYX_API_KEY"
+	EnvServerURL  = "ONYX_SERVER_URL"
+	EnvAPIKey     = "ONYX_API_KEY"
 	EnvAgentID    = "ONYX_PERSONA_ID"
+	EnvSSHHostKey = "ONYX_SSH_HOST_KEY"
 )
 
 // OnyxCliConfig holds the CLI configuration.
@@ -35,8 +36,8 @@ func (c OnyxCliConfig) IsConfigured() bool {
 	return c.APIKey != ""
 }
 
-// configDir returns ~/.config/onyx-cli
-func configDir() string {
+// ConfigDir returns ~/.config/onyx-cli
+func ConfigDir() string {
 	if xdg := os.Getenv("XDG_CONFIG_HOME"); xdg != "" {
 		return filepath.Join(xdg, "onyx-cli")
 	}
@@ -49,7 +50,7 @@ func configDir() string {
 
 // ConfigFilePath returns the full path to the config file.
 func ConfigFilePath() string {
-	return filepath.Join(configDir(), "config.json")
+	return filepath.Join(ConfigDir(), "config.json")
 }
 
 // ConfigExists checks if the config file exists on disk.
@@ -87,7 +88,7 @@ func Load() OnyxCliConfig {
 
 // Save writes the config to disk, creating parent directories if needed.
 func Save(cfg OnyxCliConfig) error {
-	dir := configDir()
+	dir := ConfigDir()
 	if err := os.MkdirAll(dir, 0o755); err != nil {
 		return err
 	}

deployment/helm/charts/onyx/Chart.yaml

@@ -5,7 +5,7 @@ home: https://www.onyx.app/
 sources:
   - "https://github.com/onyx-dot-app/onyx"
 type: application
-version: 0.4.38
+version: 0.4.39
 appVersion: latest
 annotations:
   category: Productivity

deployment/helm/charts/onyx/templates/celery-worker-servicemonitors.yaml

@@ -0,0 +1,77 @@
+{{- if and .Values.monitoring.serviceMonitors.enabled .Values.vectorDB.enabled }}
+{{- if gt (int .Values.celery_worker_monitoring.replicaCount) 0 }}
+---
+apiVersion: monitoring.coreos.com/v1
+kind: ServiceMonitor
+metadata:
+  name: {{ include "onyx.fullname" . }}-celery-worker-monitoring
+  labels:
+    {{- include "onyx.labels" . | nindent 4 }}
+    {{- with .Values.monitoring.serviceMonitors.labels }}
+    {{- toYaml . | nindent 4 }}
+    {{- end }}
+spec:
+  namespaceSelector:
+    matchNames:
+      - {{ .Release.Namespace }}
+  selector:
+    matchLabels:
+      app: {{ .Values.celery_worker_monitoring.deploymentLabels.app }}
+      metrics: "true"
+  endpoints:
+    - port: metrics
+      path: /metrics
+      interval: 30s
+      scrapeTimeout: 10s
+{{- end }}
+{{- if gt (int .Values.celery_worker_docfetching.replicaCount) 0 }}
+---
+apiVersion: monitoring.coreos.com/v1
+kind: ServiceMonitor
+metadata:
+  name: {{ include "onyx.fullname" . }}-celery-worker-docfetching
+  labels:
+    {{- include "onyx.labels" . | nindent 4 }}
+    {{- with .Values.monitoring.serviceMonitors.labels }}
+    {{- toYaml . | nindent 4 }}
+    {{- end }}
+spec:
+  namespaceSelector:
+    matchNames:
+      - {{ .Release.Namespace }}
+  selector:
+    matchLabels:
+      app: {{ .Values.celery_worker_docfetching.deploymentLabels.app }}
+      metrics: "true"
+  endpoints:
+    - port: metrics
+      path: /metrics
+      interval: 30s
+      scrapeTimeout: 10s
+{{- end }}
+{{- if gt (int .Values.celery_worker_docprocessing.replicaCount) 0 }}
+---
+apiVersion: monitoring.coreos.com/v1
+kind: ServiceMonitor
+metadata:
+  name: {{ include "onyx.fullname" . }}-celery-worker-docprocessing
+  labels:
+    {{- include "onyx.labels" . | nindent 4 }}
+    {{- with .Values.monitoring.serviceMonitors.labels }}
+    {{- toYaml . | nindent 4 }}
+    {{- end }}
+spec:
+  namespaceSelector:
+    matchNames:
+      - {{ .Release.Namespace }}
+  selector:
+    matchLabels:
+      app: {{ .Values.celery_worker_docprocessing.deploymentLabels.app }}
+      metrics: "true"
+  endpoints:
+    - port: metrics
+      path: /metrics
+      interval: 30s
+      scrapeTimeout: 10s
+{{- end }}
+{{- end }}

deployment/helm/charts/onyx/templates/grafana-dashboards.yaml

@@ -0,0 +1,15 @@
+{{- if .Values.monitoring.grafana.dashboards.enabled }}
+---
+apiVersion: v1
+kind: ConfigMap
+metadata:
+  name: {{ include "onyx.fullname" . }}-indexing-pipeline-dashboard
+  labels:
+    {{- include "onyx.labels" . | nindent 4 }}
+    grafana_dashboard: "1"
+  annotations:
+    grafana_folder: "Onyx"
+data:
+  onyx-indexing-pipeline.json: |
+    {{- .Files.Get "dashboards/indexing-pipeline.json" | nindent 4 }}
+{{- end }}

deployment/helm/charts/onyx/values.yaml

@@ -256,6 +256,20 @@ tooling:
     # -- Which client binary to call; change if your image uses a non-default path.
     psqlBinary: psql
 
+monitoring:
+  grafana:
+    dashboards:
+      # -- Set to true to deploy Grafana dashboard ConfigMaps for the Onyx indexing pipeline.
+      # Requires kube-prometheus-stack (or equivalent) with the Grafana sidecar enabled and watching this namespace.
+      # The sidecar must be configured with label selector: grafana_dashboard=1
+      enabled: false
+  serviceMonitors:
+    # -- Set to true to deploy ServiceMonitor resources for Celery worker metrics endpoints.
+    # Requires the Prometheus Operator CRDs (included in kube-prometheus-stack).
+    # Use `labels` to match your Prometheus CR's serviceMonitorSelector (e.g. release: onyx-monitoring).
+    enabled: false
+    labels: {}
+
 serviceAccount:
   # Specifies whether a service account should be created
   create: false

deployment/terraform/modules/aws/eks/main.tf

@@ -19,6 +19,10 @@ module "eks" {
   cluster_endpoint_public_access_cidrs     = var.cluster_endpoint_public_access_cidrs
   enable_cluster_creator_admin_permissions = true
 
+  # Control plane logging
+  cluster_enabled_log_types              = var.cluster_enabled_log_types
+  cloudwatch_log_group_retention_in_days = var.cloudwatch_log_group_retention_in_days
+
   eks_managed_node_group_defaults = {
     ami_type = "AL2023_x86_64_STANDARD"
   }

deployment/terraform/modules/aws/eks/variables.tf

@@ -161,3 +161,25 @@ variable "rds_db_connect_arn" {
   description = "Full rds-db:connect ARN to allow (required when enable_rds_iam_for_service_account is true)"
   default     = null
 }
+
+variable "cluster_enabled_log_types" {
+  type        = list(string)
+  description = "EKS control plane log types to enable (valid: api, audit, authenticator, controllerManager, scheduler)"
+  default     = ["api", "audit", "authenticator", "controllerManager", "scheduler"]
+
+  validation {
+    condition     = alltrue([for t in var.cluster_enabled_log_types : contains(["api", "audit", "authenticator", "controllerManager", "scheduler"], t)])
+    error_message = "Each entry must be one of: api, audit, authenticator, controllerManager, scheduler."
+  }
+}
+
+variable "cloudwatch_log_group_retention_in_days" {
+  type        = number
+  description = "Number of days to retain EKS control plane logs in CloudWatch (0 = never expire)"
+  default     = 30
+
+  validation {
+    condition     = contains([0, 1, 3, 5, 7, 14, 30, 60, 90, 120, 150, 180, 365, 400, 545, 731, 1096, 1827, 2192, 2557, 2922, 3288, 3653], var.cloudwatch_log_group_retention_in_days)
+    error_message = "Must be a valid CloudWatch retention value (0, 1, 3, 5, 7, 14, 30, 60, 90, 120, 150, 180, 365, 400, 545, 731, 1096, 1827, 2192, 2557, 2922, 3288, 3653)."
+  }
+}

deployment/terraform/modules/aws/onyx/main.tf

@@ -54,6 +54,9 @@ module "postgres" {
   password            = var.postgres_password
   tags                = local.merged_tags
   enable_rds_iam_auth = var.enable_iam_auth
+
+  backup_retention_period = var.postgres_backup_retention_period
+  backup_window           = var.postgres_backup_window
 }
 
 module "s3" {
@@ -80,6 +83,10 @@ module "eks" {
   public_cluster_enabled               = var.public_cluster_enabled
   private_cluster_enabled              = var.private_cluster_enabled
   cluster_endpoint_public_access_cidrs = var.cluster_endpoint_public_access_cidrs
+
+  # Control plane logging
+  cluster_enabled_log_types              = var.eks_cluster_enabled_log_types
+  cloudwatch_log_group_retention_in_days = var.eks_cloudwatch_log_group_retention_in_days
 }
 
 module "waf" {

deployment/terraform/modules/aws/onyx/variables.tf

@@ -250,3 +250,34 @@ variable "opensearch_subnet_ids" {
   description = "Subnet IDs for OpenSearch. If empty, uses first 3 private subnets."
   default     = []
 }
+
+# RDS Backup Configuration
+variable "postgres_backup_retention_period" {
+  type        = number
+  description = "Number of days to retain automated RDS backups (0 to disable)"
+  default     = 7
+}
+
+variable "postgres_backup_window" {
+  type        = string
+  description = "Preferred UTC time window for automated RDS backups (hh24:mi-hh24:mi)"
+  default     = "03:00-04:00"
+}
+
+# EKS Control Plane Logging
+variable "eks_cluster_enabled_log_types" {
+  type        = list(string)
+  description = "EKS control plane log types to enable (valid: api, audit, authenticator, controllerManager, scheduler)"
+  default     = ["api", "audit", "authenticator", "controllerManager", "scheduler"]
+}
+
+variable "eks_cloudwatch_log_group_retention_in_days" {
+  type        = number
+  description = "Number of days to retain EKS control plane logs in CloudWatch (0 = never expire)"
+  default     = 30
+
+  validation {
+    condition     = contains([0, 1, 3, 5, 7, 14, 30, 60, 90, 120, 150, 180, 365, 400, 545, 731, 1096, 1827, 2192, 2557, 2922, 3288, 3653], var.eks_cloudwatch_log_group_retention_in_days)
+    error_message = "Must be a valid CloudWatch retention value (0, 1, 3, 5, 7, 14, 30, 60, 90, 120, 150, 180, 365, 400, 545, 731, 1096, 1827, 2192, 2557, 2922, 3288, 3653)."
+  }
+}

deployment/terraform/modules/aws/postgres/main.tf

@@ -44,5 +44,56 @@ resource "aws_db_instance" "this" {
   publicly_accessible    = false
   deletion_protection    = true
   storage_encrypted      = true
-  tags                   = var.tags
+
+  # Automated backups
+  backup_retention_period = var.backup_retention_period
+  backup_window           = var.backup_window
+
+  tags = var.tags
+}
+
+# CloudWatch alarm for CPU utilization monitoring
+resource "aws_cloudwatch_metric_alarm" "cpu_utilization" {
+  alarm_name          = "${var.identifier}-cpu-utilization"
+  alarm_description   = "RDS CPU utilization for ${var.identifier}"
+  comparison_operator = "GreaterThanThreshold"
+  evaluation_periods  = var.cpu_alarm_evaluation_periods
+  metric_name         = "CPUUtilization"
+  namespace           = "AWS/RDS"
+  period              = var.cpu_alarm_period
+  statistic           = "Average"
+  threshold           = var.cpu_alarm_threshold
+  treat_missing_data  = "missing"
+
+  alarm_actions = var.alarm_actions
+  ok_actions    = var.alarm_actions
+
+  dimensions = {
+    DBInstanceIdentifier = aws_db_instance.this.identifier
+  }
+
+  tags = var.tags
+}
+
+# CloudWatch alarm for freeable memory monitoring
+resource "aws_cloudwatch_metric_alarm" "freeable_memory" {
+  alarm_name          = "${var.identifier}-freeable-memory"
+  alarm_description   = "RDS freeable memory for ${var.identifier}"
+  comparison_operator = "LessThanThreshold"
+  evaluation_periods  = var.memory_alarm_evaluation_periods
+  metric_name         = "FreeableMemory"
+  namespace           = "AWS/RDS"
+  period              = var.memory_alarm_period
+  statistic           = "Average"
+  threshold           = var.memory_alarm_threshold
+  treat_missing_data  = "missing"
+
+  alarm_actions = var.alarm_actions
+  ok_actions    = var.alarm_actions
+
+  dimensions = {
+    DBInstanceIdentifier = aws_db_instance.this.identifier
+  }
+
+  tags = var.tags
 }

deployment/terraform/modules/aws/postgres/variables.tf

@@ -67,3 +67,98 @@ variable "enable_rds_iam_auth" {
   description = "Enable AWS IAM database authentication for this RDS instance"
   default     = false
 }
+
+variable "backup_retention_period" {
+  type        = number
+  description = "Number of days to retain automated backups (0 to disable)"
+  default     = 7
+
+  validation {
+    condition     = var.backup_retention_period >= 0 && var.backup_retention_period <= 35
+    error_message = "backup_retention_period must be between 0 and 35 (AWS RDS limit)."
+  }
+}
+
+variable "backup_window" {
+  type        = string
+  description = "Preferred UTC time window for automated backups (hh24:mi-hh24:mi)"
+  default     = "03:00-04:00"
+
+  validation {
+    condition     = can(regex("^([01]\\d|2[0-3]):[0-5]\\d-([01]\\d|2[0-3]):[0-5]\\d$", var.backup_window))
+    error_message = "backup_window must be in hh24:mi-hh24:mi format (e.g. \"03:00-04:00\")."
+  }
+}
+
+# CloudWatch CPU alarm configuration
+variable "cpu_alarm_threshold" {
+  type        = number
+  description = "CPU utilization percentage threshold for the CloudWatch alarm"
+  default     = 80
+
+  validation {
+    condition     = var.cpu_alarm_threshold >= 0 && var.cpu_alarm_threshold <= 100
+    error_message = "cpu_alarm_threshold must be between 0 and 100 (percentage)."
+  }
+}
+
+variable "cpu_alarm_evaluation_periods" {
+  type        = number
+  description = "Number of consecutive periods the threshold must be breached before alarming"
+  default     = 3
+
+  validation {
+    condition     = var.cpu_alarm_evaluation_periods >= 1
+    error_message = "cpu_alarm_evaluation_periods must be at least 1."
+  }
+}
+
+variable "cpu_alarm_period" {
+  type        = number
+  description = "Period in seconds over which the CPU metric is evaluated"
+  default     = 300
+
+  validation {
+    condition     = var.cpu_alarm_period >= 60 && var.cpu_alarm_period % 60 == 0
+    error_message = "cpu_alarm_period must be a multiple of 60 seconds and at least 60 (CloudWatch requirement)."
+  }
+}
+
+variable "memory_alarm_threshold" {
+  type        = number
+  description = "Freeable memory threshold in bytes. Alarm fires when memory drops below this value."
+  default     = 256000000 # 256 MB
+
+  validation {
+    condition     = var.memory_alarm_threshold > 0
+    error_message = "memory_alarm_threshold must be greater than 0."
+  }
+}
+
+variable "memory_alarm_evaluation_periods" {
+  type        = number
+  description = "Number of consecutive periods the threshold must be breached before alarming"
+  default     = 3
+
+  validation {
+    condition     = var.memory_alarm_evaluation_periods >= 1
+    error_message = "memory_alarm_evaluation_periods must be at least 1."
+  }
+}
+
+variable "memory_alarm_period" {
+  type        = number
+  description = "Period in seconds over which the freeable memory metric is evaluated"
+  default     = 300
+
+  validation {
+    condition     = var.memory_alarm_period >= 60 && var.memory_alarm_period % 60 == 0
+    error_message = "memory_alarm_period must be a multiple of 60 seconds and at least 60 (CloudWatch requirement)."
+  }
+}
+
+variable "alarm_actions" {
+  type        = list(string)
+  description = "List of ARNs to notify when the alarm transitions state (e.g. SNS topic ARNs)"
+  default     = []
+}

pyproject.toml

@@ -66,7 +66,7 @@ backend = [
     "jsonref==1.1.0",
     "kubernetes==31.0.0",
     "trafilatura==1.12.2",
-    "langchain-core==1.2.11",
+    "langchain-core==1.2.22",
     "lazy_imports==1.0.1",
     "lxml==5.3.0",
     "Mako==1.2.4",

uv.lock

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 [[package]]
@@ -3048,7 +3048,7 @@ wheels = [
 
 [[package]]
 name = "langchain-core"
-version = "1.2.11"
+version = "1.2.22"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "jsonpatch" },
@@ -3060,9 +3060,9 @@ dependencies = [
     { name = "typing-extensions" },
     { name = "uuid-utils" },
 ]
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@@ -4439,7 +4439,7 @@ requires-dist = [
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     { name = "kubernetes", specifier = ">=31.0.0" },
     { name = "kubernetes", marker = "extra == 'backend'", specifier = "==31.0.0" },
-    { name = "langchain-core", marker = "extra == 'backend'", specifier = "==1.2.11" },
+    { name = "langchain-core", marker = "extra == 'backend'", specifier = "==1.2.22" },
     { name = "langfuse", marker = "extra == 'backend'", specifier = "==3.10.0" },
     { name = "lazy-imports", marker = "extra == 'backend'", specifier = "==1.0.1" },
     { name = "litellm", specifier = "==1.81.6" },
@@ -5634,11 +5634,11 @@ wheels = [
 
 [[package]]
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-version = "2.19.2"
+version = "2.20.0"
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 [[package]]

web/Dockerfile

@@ -73,11 +73,17 @@ ENV NEXT_PUBLIC_STRIPE_PUBLISHABLE_KEY=${NEXT_PUBLIC_STRIPE_PUBLISHABLE_KEY}
 ARG NEXT_PUBLIC_RECAPTCHA_SITE_KEY
 ENV NEXT_PUBLIC_RECAPTCHA_SITE_KEY=${NEXT_PUBLIC_RECAPTCHA_SITE_KEY}
 
+ARG SENTRY_RELEASE
+ENV SENTRY_RELEASE=${SENTRY_RELEASE}
+
 # Add NODE_OPTIONS argument
 ARG NODE_OPTIONS
 
+# SENTRY_AUTH_TOKEN is injected via BuildKit secret mount so it is never written
+# to any image layer, build cache, or registry manifest.
 # Use NODE_OPTIONS in the build command
-RUN NODE_OPTIONS="${NODE_OPTIONS}" npx next build
+RUN --mount=type=secret,id=sentry_auth_token,env=SENTRY_AUTH_TOKEN \
+    NODE_OPTIONS="${NODE_OPTIONS}" npx next build
 
 # Step 2. Production image, copy all the files and run next
 FROM base AS runner
@@ -150,6 +156,9 @@ ENV NEXT_PUBLIC_STRIPE_PUBLISHABLE_KEY=${NEXT_PUBLIC_STRIPE_PUBLISHABLE_KEY}
 ARG NEXT_PUBLIC_RECAPTCHA_SITE_KEY
 ENV NEXT_PUBLIC_RECAPTCHA_SITE_KEY=${NEXT_PUBLIC_RECAPTCHA_SITE_KEY}
 
+ARG SENTRY_RELEASE
+ENV SENTRY_RELEASE=${SENTRY_RELEASE}
+
 # Default ONYX_VERSION, typically overriden during builds by GitHub Actions.
 ARG ONYX_VERSION=0.0.0-dev
 ENV ONYX_VERSION=${ONYX_VERSION}

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

@@ -104,7 +104,7 @@ function Button({
           isLarge ? "default" : size === "2xs" ? "mini" : "compact"
         }
       >
-        <div className="flex flex-row items-center gap-1 interactive-foreground">
+        <div className="flex flex-row items-center gap-1">
           {iconWrapper(Icon, size, !!children)}
 
           {labelEl}

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

@@ -67,7 +67,7 @@ function FilterButton({
         state={active ? "selected" : "empty"}
       >
         <Interactive.Container type="button">
-          <div className="interactive-foreground flex flex-row items-center gap-1">
+          <div className="flex flex-row items-center gap-1">
             {iconWrapper(Icon, "lg", true)}
             <Text font="main-ui-action" color="inherit" nowrap>
               {children}

web/lib/opal/src/components/buttons/line-item-button/components.tsx

@@ -16,7 +16,7 @@ import * as TooltipPrimitive from "@radix-ui/react-tooltip";
 
 type ContentPassthroughProps = DistributiveOmit<
   ContentActionProps,
-  "paddingVariant" | "widthVariant" | "ref" | "withInteractive"
+  "paddingVariant" | "widthVariant" | "ref"
 >;
 
 type LineItemButtonOwnProps = Pick<
@@ -92,7 +92,6 @@ function LineItemButton({
       >
         <ContentAction
           {...(contentActionProps as ContentActionProps)}
-          withInteractive
           paddingVariant="fit"
         />
       </Interactive.Container>

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

@@ -132,7 +132,7 @@ function OpenButton({
       >
         <div
           className={cn(
-            "interactive-foreground flex flex-row items-center",
+            "flex flex-row items-center",
             justifyContent === "between" ? "w-full justify-between" : "gap-1",
             foldable &&
               justifyContent !== "between" &&

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

@@ -1,3 +1,5 @@
+"use client";
+
 import "@opal/components/buttons/select-button/styles.css";
 import {
   Interactive,
@@ -84,11 +86,13 @@ function SelectButton({
   const isLarge = size === "lg";
 
   const labelEl = children ? (
-    <span className="opal-select-button-label">
-      <Text font={isLarge ? "main-ui-body" : "secondary-body"} color="inherit">
-        {children}
-      </Text>
-    </span>
+    <Text
+      font={isLarge ? "main-ui-body" : "secondary-body"}
+      color="inherit"
+      nowrap
+    >
+      {children}
+    </Text>
   ) : null;
 
   const button = (
@@ -103,7 +107,7 @@ function SelectButton({
       >
         <div
           className={cn(
-            "opal-select-button interactive-foreground",
+            "opal-select-button",
             foldable && "interactive-foldable-host"
           )}
         >

web/lib/opal/src/components/buttons/select-button/styles.css

@@ -3,7 +3,3 @@
 .opal-select-button {
   @apply flex flex-row items-center gap-1;
 }
-
-.opal-select-button-label {
-  @apply whitespace-nowrap;
-}

web/lib/opal/src/components/cards/select-card/README.md

@@ -0,0 +1,136 @@
+# SelectCard
+
+**Import:** `import { SelectCard, type SelectCardProps } from "@opal/components";`
+
+A stateful interactive card — the card counterpart to [`SelectButton`](../../buttons/select-button/README.md). Built on `Interactive.Stateful` (Slot) with a structural `<div>` that owns padding, rounding, border, and overflow.
+
+## Relationship to Card
+
+`Card` is a plain, non-interactive container. `SelectCard` adds stateful interactivity (hover, active, disabled, state-driven colors) by wrapping its root div with `Interactive.Stateful`. The relationship mirrors `Button` (stateless) vs `SelectButton` (stateful).
+
+## Relationship to SelectButton
+
+SelectCard and SelectButton share the same call stack:
+
+```
+Interactive.Stateful → structural element → content
+```
+
+The key differences:
+
+- SelectCard renders a `<div>` (not `Interactive.Container`) — cards have their own rounding scale (one notch larger than buttons) and don't need Container's height/min-width.
+- SelectCard has no `foldable` prop — use `Interactive.Foldable` directly inside children.
+- SelectCard's children are fully composable — use `CardHeaderLayout`, `ContentAction`, `Content`, buttons, etc. inside.
+
+## Architecture
+
+```
+Interactive.Stateful              <- variant, state, interaction, disabled, onClick
+  └─ div.opal-select-card        <- padding, rounding, border, overflow
+       └─ children (composable)
+```
+
+The `Interactive.Stateful` Slot merges onto the div, producing a single DOM element with both `.opal-select-card` and `.interactive` classes plus `data-interactive-*` attributes. This activates the Stateful color matrix for backgrounds and `--interactive-foreground` / `--interactive-foreground-icon` CSS properties for descendants.
+
+## Props
+
+Inherits **all** props from `InteractiveStatefulProps` (variant, state, interaction, onClick, href, etc.) plus:
+
+| Prop | Type | Default | Description |
+|---|---|---|---|
+| `sizeVariant` | `ContainerSizeVariants` | `"lg"` | Controls padding and border-radius |
+| `ref` | `React.Ref<HTMLDivElement>` | — | Ref forwarded to the root div |
+| `children` | `React.ReactNode` | — | Card content |
+
+### Rounding scale
+
+Cards use a bumped-up rounding scale compared to buttons:
+
+| Size | Rounding | Effective radius |
+|---|---|---|
+| `lg` | `rounded-16` | 1rem (16px) |
+| `md`–`sm` | `rounded-12` | 0.75rem (12px) |
+| `xs`–`2xs` | `rounded-08` | 0.5rem (8px) |
+| `fit` | `rounded-16` | 1rem (16px) |
+
+### Recommended variant: `select-card`
+
+The `select-card` Interactive.Stateful variant is specifically designed for cards. Unlike `select-heavy` (which only changes foreground color between empty and filled), `select-card` gives the filled state a visible background — important on larger surfaces where background carries more of the visual distinction.
+
+| State | Rest background | Rest foreground |
+|---|---|---|
+| `empty` | transparent | `text-04` / icon `text-03` |
+| `filled` | `background-tint-00` | `text-04` / icon `text-03` |
+| `selected` | `action-link-01` | `action-link-05` |
+
+The selected state also gets a `border-action-link-05` via SelectCard's CSS.
+
+## CSS
+
+SelectCard's stylesheet (`styles.css`) provides:
+
+- `w-full overflow-clip border` on all states
+- `border-action-link-05` when `data-interactive-state="selected"`
+
+All background and foreground colors come from the Interactive.Stateful CSS, not from SelectCard.
+
+## Usage
+
+### Provider selection card
+
+```tsx
+import { SelectCard } from "@opal/components";
+import { CardHeaderLayout } from "@opal/layouts";
+
+<SelectCard variant="select-card" state="selected" onClick={handleClick}>
+  <CardHeaderLayout
+    icon={SvgGlobe}
+    title="Google"
+    description="Search engine"
+    sizePreset="main-ui"
+    variant="section"
+    rightChildren={<Button icon={SvgCheckSquare} variant="action" prominence="tertiary">Current Default</Button>}
+    bottomRightChildren={
+      <Button icon={SvgSettings} size="sm" prominence="tertiary" />
+    }
+  />
+</SelectCard>
+```
+
+### Disconnected state (clickable)
+
+```tsx
+<SelectCard variant="select-card" state="empty" onClick={handleConnect}>
+  <CardHeaderLayout
+    icon={SvgCloud}
+    title="OpenAI"
+    description="Not configured"
+    sizePreset="main-ui"
+    variant="section"
+    rightChildren={<Button rightIcon={SvgArrowExchange} prominence="tertiary">Connect</Button>}
+  />
+</SelectCard>
+```
+
+### With foldable hover-reveal
+
+```tsx
+<SelectCard variant="select-card" state="filled">
+  <CardHeaderLayout
+    icon={SvgCloud}
+    title="OpenAI"
+    description="Connected"
+    sizePreset="main-ui"
+    variant="section"
+    rightChildren={
+      <div className="interactive-foldable-host flex items-center">
+        <Interactive.Foldable>
+          <Button rightIcon={SvgArrowRightCircle} prominence="tertiary">
+            Set as Default
+          </Button>
+        </Interactive.Foldable>
+      </div>
+    }
+  />
+</SelectCard>
+```

web/lib/opal/src/components/cards/select-card/SelectCard.stories.tsx

@@ -0,0 +1,247 @@
+import type { Meta, StoryObj } from "@storybook/react";
+import { SelectCard } from "@opal/components";
+import { Button } from "@opal/components";
+import { Content } from "@opal/layouts";
+import {
+  SvgArrowExchange,
+  SvgArrowRightCircle,
+  SvgCheckSquare,
+  SvgGlobe,
+  SvgSettings,
+  SvgUnplug,
+} from "@opal/icons";
+import { Interactive } from "@opal/core";
+import * as TooltipPrimitive from "@radix-ui/react-tooltip";
+import type { Decorator } from "@storybook/react";
+
+const withTooltipProvider: Decorator = (Story) => (
+  <TooltipPrimitive.Provider>
+    <Story />
+  </TooltipPrimitive.Provider>
+);
+
+const STATES = ["empty", "filled", "selected"] as const;
+const SIZE_VARIANTS = ["lg", "md", "sm", "xs", "2xs", "fit"] as const;
+
+const meta = {
+  title: "opal/components/SelectCard",
+  component: SelectCard,
+  tags: ["autodocs"],
+  decorators: [withTooltipProvider],
+  parameters: {
+    layout: "centered",
+  },
+} satisfies Meta<typeof SelectCard>;
+
+export default meta;
+
+type Story = StoryObj<typeof meta>;
+
+// ---------------------------------------------------------------------------
+// Stories
+// ---------------------------------------------------------------------------
+
+export const Default: Story = {
+  render: () => (
+    <div className="w-96">
+      <SelectCard variant="select-card" state="empty">
+        <div className="p-2">
+          <Content
+            sizePreset="main-ui"
+            variant="section"
+            icon={SvgGlobe}
+            title="Google Search"
+            description="Web search provider"
+          />
+        </div>
+      </SelectCard>
+    </div>
+  ),
+};
+
+export const AllStates: Story = {
+  render: () => (
+    <div className="flex flex-col gap-4 w-96">
+      {STATES.map((state) => (
+        <SelectCard key={state} variant="select-card" state={state}>
+          <div className="p-2">
+            <Content
+              sizePreset="main-ui"
+              variant="section"
+              icon={SvgGlobe}
+              title={`State: ${state}`}
+              description="Hover to see interaction states."
+            />
+          </div>
+        </SelectCard>
+      ))}
+    </div>
+  ),
+};
+
+export const Clickable: Story = {
+  render: () => (
+    <div className="w-96">
+      <SelectCard
+        variant="select-card"
+        state="empty"
+        onClick={() => alert("Card clicked")}
+      >
+        <div className="p-2">
+          <Content
+            sizePreset="main-ui"
+            variant="section"
+            icon={SvgGlobe}
+            title="Clickable Card"
+            description="Click anywhere on this card."
+          />
+        </div>
+      </SelectCard>
+    </div>
+  ),
+};
+
+export const WithActions: Story = {
+  render: () => (
+    <div className="flex flex-col gap-4 w-[28rem]">
+      {/* Disconnected */}
+      <SelectCard variant="select-card" state="empty" onClick={() => {}}>
+        <div className="flex flex-row items-stretch w-full">
+          <div className="flex-1 p-2">
+            <Content
+              sizePreset="main-ui"
+              variant="section"
+              icon={SvgGlobe}
+              title="Disconnected"
+              description="Click to connect."
+            />
+          </div>
+          <div className="flex items-center">
+            <Button prominence="tertiary" rightIcon={SvgArrowExchange}>
+              Connect
+            </Button>
+          </div>
+        </div>
+      </SelectCard>
+
+      {/* Connected with foldable */}
+      <SelectCard variant="select-card" state="filled">
+        <div className="flex flex-row items-stretch w-full">
+          <div className="flex-1 p-2">
+            <Content
+              sizePreset="main-ui"
+              variant="section"
+              icon={SvgGlobe}
+              title="Connected"
+              description="Hover to reveal Set as Default."
+            />
+          </div>
+          <div className="flex flex-col items-end justify-between">
+            <div className="interactive-foldable-host flex items-center">
+              <Interactive.Foldable>
+                <Button prominence="tertiary" rightIcon={SvgArrowRightCircle}>
+                  Set as Default
+                </Button>
+              </Interactive.Foldable>
+            </div>
+            <div className="flex flex-row px-1 pb-1">
+              <Button
+                icon={SvgUnplug}
+                tooltip="Disconnect"
+                prominence="tertiary"
+                size="sm"
+              />
+              <Button
+                icon={SvgSettings}
+                tooltip="Edit"
+                prominence="tertiary"
+                size="sm"
+              />
+            </div>
+          </div>
+        </div>
+      </SelectCard>
+
+      {/* Selected */}
+      <SelectCard variant="select-card" state="selected">
+        <div className="flex flex-row items-stretch w-full">
+          <div className="flex-1 p-2">
+            <Content
+              sizePreset="main-ui"
+              variant="section"
+              icon={SvgGlobe}
+              title="Selected"
+              description="Currently the default provider."
+            />
+          </div>
+          <div className="flex flex-col items-end justify-between">
+            <Button
+              variant="action"
+              prominence="tertiary"
+              icon={SvgCheckSquare}
+            >
+              Current Default
+            </Button>
+            <div className="flex flex-row px-1 pb-1">
+              <Button
+                icon={SvgUnplug}
+                tooltip="Disconnect"
+                prominence="tertiary"
+                size="sm"
+              />
+              <Button
+                icon={SvgSettings}
+                tooltip="Edit"
+                prominence="tertiary"
+                size="sm"
+              />
+            </div>
+          </div>
+        </div>
+      </SelectCard>
+    </div>
+  ),
+};
+
+export const SizeVariants: Story = {
+  render: () => (
+    <div className="flex flex-col gap-4 w-96">
+      {SIZE_VARIANTS.map((size) => (
+        <SelectCard
+          key={size}
+          variant="select-card"
+          state="filled"
+          sizeVariant={size}
+        >
+          <Content
+            sizePreset="main-ui"
+            variant="section"
+            icon={SvgGlobe}
+            title={`sizeVariant: ${size}`}
+            description="Shows padding and rounding differences."
+          />
+        </SelectCard>
+      ))}
+    </div>
+  ),
+};
+
+export const SelectHeavyVariant: Story = {
+  render: () => (
+    <div className="flex flex-col gap-4 w-96">
+      {STATES.map((state) => (
+        <SelectCard key={state} variant="select-heavy" state={state}>
+          <div className="p-2">
+            <Content
+              sizePreset="main-ui"
+              variant="section"
+              icon={SvgGlobe}
+              title={`select-heavy / ${state}`}
+              description="For comparison with select-card variant."
+            />
+          </div>
+        </SelectCard>
+      ))}
+    </div>
+  ),
+};

web/lib/opal/src/components/cards/select-card/components.tsx

@@ -0,0 +1,96 @@
+import "@opal/components/cards/select-card/styles.css";
+import type { ContainerSizeVariants } from "@opal/types";
+import { containerSizeVariants } from "@opal/shared";
+import { cn } from "@opal/utils";
+import { Interactive, type InteractiveStatefulProps } from "@opal/core";
+
+// ---------------------------------------------------------------------------
+// Types
+// ---------------------------------------------------------------------------
+
+type SelectCardProps = InteractiveStatefulProps & {
+  /**
+   * Size preset — controls padding and border-radius.
+   *
+   * Padding comes from the shared size scale. Rounding follows the same
+   * mapping as `Card` / `Button` / `Interactive.Container`:
+   *
+   * | Size       | Rounding     |
+   * |------------|--------------|
+   * | `lg`       | `rounded-16` |
+   * | `md`–`sm`  | `rounded-12` |
+   * | `xs`–`2xs` | `rounded-08` |
+   * | `fit`      | `rounded-16` |
+   *
+   * @default "lg"
+   */
+  sizeVariant?: ContainerSizeVariants;
+
+  /** Ref forwarded to the root `<div>`. */
+  ref?: React.Ref<HTMLDivElement>;
+
+  children?: React.ReactNode;
+};
+
+// ---------------------------------------------------------------------------
+// Rounding
+// ---------------------------------------------------------------------------
+
+const roundingForSize: Record<ContainerSizeVariants, string> = {
+  lg: "rounded-16",
+  md: "rounded-12",
+  sm: "rounded-12",
+  xs: "rounded-08",
+  "2xs": "rounded-08",
+  fit: "rounded-16",
+};
+
+// ---------------------------------------------------------------------------
+// SelectCard
+// ---------------------------------------------------------------------------
+
+/**
+ * A stateful interactive card — the card counterpart to `SelectButton`.
+ *
+ * Built on `Interactive.Stateful` (Slot) → a structural `<div>`. The
+ * Stateful system owns background and foreground colors; the card owns
+ * padding, rounding, border, and overflow.
+ *
+ * Children are fully composable — use `ContentAction`, `Content`, buttons,
+ * `Interactive.Foldable`, etc. inside.
+ *
+ * @example
+ * ```tsx
+ * <SelectCard variant="select-card" state="selected" onClick={handleClick}>
+ *   <ContentAction
+ *     icon={SvgGlobe}
+ *     title="Google"
+ *     description="Search engine"
+ *     rightChildren={<Button>Set as Default</Button>}
+ *   />
+ * </SelectCard>
+ * ```
+ */
+function SelectCard({
+  sizeVariant = "lg",
+  ref,
+  children,
+  ...statefulProps
+}: SelectCardProps) {
+  const { padding } = containerSizeVariants[sizeVariant];
+  const rounding = roundingForSize[sizeVariant];
+
+  return (
+    <Interactive.Stateful {...statefulProps}>
+      <div ref={ref} className={cn("opal-select-card", padding, rounding)}>
+        {children}
+      </div>
+    </Interactive.Stateful>
+  );
+}
+
+// ---------------------------------------------------------------------------
+// Exports
+// ---------------------------------------------------------------------------
+
+export { SelectCard, type SelectCardProps };

web/lib/opal/src/components/cards/select-card/styles.css

@@ -0,0 +1,9 @@
+/* SelectCard — structural styles; colors handled by Interactive.Stateful */
+
+.opal-select-card {
+  @apply w-full overflow-clip border;
+}
+
+.opal-select-card[data-interactive-state="selected"] {
+  @apply border-action-link-05;
+}

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

@@ -56,6 +56,12 @@ export {
   type BorderVariant,
 } from "@opal/components/cards/card/components";
 
+/* SelectCard */
+export {
+  SelectCard,
+  type SelectCardProps,
+} from "@opal/components/cards/select-card/components";
+
 /* EmptyMessageCard */
 export {
   EmptyMessageCard,

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

@@ -390,14 +390,12 @@ function PaginationCount({
         <span className={textClasses(size, "muted")}>of</span>
         {totalItems}
         {units && (
-          <span className="ml-1">
-            <Text
-              color="inherit"
-              font={size === "sm" ? "secondary-body" : "main-ui-muted"}
-            >
-              {units}
-            </Text>
-          </span>
+          <Text
+            color="inherit"
+            font={size === "sm" ? "secondary-body" : "main-ui-muted"}
+          >
+            {units}
+          </Text>
         )}
       </span>
 

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

@@ -1,5 +1,4 @@
 import "@opal/components/tag/styles.css";
-
 import type { IconFunctionComponent, RichStr } from "@opal/types";
 import { Text } from "@opal/components";
 import { cn } from "@opal/utils";
@@ -46,20 +45,22 @@ function Tag({ icon: Icon, title, color = "gray", size = "sm" }: TagProps) {
   const config = COLOR_CONFIG[color];
 
   return (
-    <div className={cn("opal-auxiliary-tag", config.bg)} data-size={size}>
+    <div
+      className={cn("opal-auxiliary-tag", config.bg, config.text)}
+      data-size={size}
+    >
       {Icon && (
         <div className="opal-auxiliary-tag-icon-container">
           <Icon className={cn("opal-auxiliary-tag-icon", config.text)} />
         </div>
       )}
-      <span className={cn("opal-auxiliary-tag-title px-[2px]", config.text)}>
-        <Text
-          font={size === "md" ? "secondary-body" : "figure-small-value"}
-          color="inherit"
-        >
-          {title}
-        </Text>
-      </span>
+      <Text
+        font={size === "md" ? "secondary-body" : "figure-small-value"}
+        color="inherit"
+        nowrap
+      >
+        {title}
+      </Text>
     </div>
   );
 }

web/lib/opal/src/components/text/InlineMarkdown.tsx

@@ -13,7 +13,9 @@ const SAFE_PROTOCOL = /^https?:|^mailto:|^tel:/i;
 const ALLOWED_ELEMENTS = ["p", "br", "a", "strong", "em", "code", "del"];
 
 const INLINE_COMPONENTS = {
-  p: ({ children }: { children?: ReactNode }) => <>{children}</>,
+  p: ({ children }: { children?: ReactNode }) => (
+    <span className="block">{children}</span>
+  ),
   a: ({ children, href }: { children?: ReactNode; href?: string }) => {
     if (!href || !SAFE_PROTOCOL.test(href)) {
       return <>{children}</>;

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

@@ -125,6 +125,7 @@ function Text({
   ...rest
 }: TextProps) {
   const resolvedClassName = cn(
+    "px-[2px]",
     FONT_CONFIG[font],
     COLOR_CONFIG[color],
     nowrap && "whitespace-nowrap",

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

@@ -18,9 +18,11 @@ export {
 import { InteractiveStateless } from "@opal/core/interactive/stateless/components";
 import { InteractiveStateful } from "@opal/core/interactive/stateful/components";
 import { InteractiveContainer } from "@opal/core/interactive/container/components";
+import { InteractiveSimple } from "@opal/core/interactive/simple/components";
 import { Foldable } from "@opal/core/interactive/foldable/components";
 
 const Interactive = {
+  Simple: InteractiveSimple,
   Stateless: InteractiveStateless,
   Stateful: InteractiveStateful,
   Container: InteractiveContainer,
@@ -50,3 +52,5 @@ export type {
 } from "@opal/core/interactive/container/components";
 
 export type { FoldableProps } from "@opal/core/interactive/foldable/components";
+
+export type { InteractiveSimpleProps } from "@opal/core/interactive/simple/components";

web/lib/opal/src/core/interactive/Interactive.stories.tsx

@@ -9,7 +9,6 @@ const VARIANT_PROMINENCE_MAP: Record<string, string[]> = {
   default: ["primary", "secondary", "tertiary", "internal"],
   action: ["primary", "secondary", "tertiary", "internal"],
   danger: ["primary", "secondary", "tertiary", "internal"],
-  none: [],
 };
 
 const SIZE_VARIANTS = ["lg", "md", "sm", "xs", "2xs", "fit"] as const;
@@ -43,7 +42,7 @@ export const Default: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">Secondary</span>
+          <span>Secondary</span>
         </Interactive.Container>
       </Interactive.Stateless>
 
@@ -53,7 +52,7 @@ export const Default: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">Primary</span>
+          <span>Primary</span>
         </Interactive.Container>
       </Interactive.Stateless>
 
@@ -63,7 +62,7 @@ export const Default: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">Tertiary</span>
+          <span>Tertiary</span>
         </Interactive.Container>
       </Interactive.Stateless>
     </div>
@@ -115,9 +114,7 @@ export const VariantMatrix: StoryObj = {
                     onClick={() => {}}
                   >
                     <Interactive.Container border>
-                      <span className="interactive-foreground">
-                        {prominence}
-                      </span>
+                      <span>{prominence}</span>
                     </Interactive.Container>
                   </Interactive.Stateless>
                   <span
@@ -150,7 +147,7 @@ export const Sizes: StoryObj = {
           onClick={() => {}}
         >
           <Interactive.Container border heightVariant={size}>
-            <span className="interactive-foreground">{size}</span>
+            <span>{size}</span>
           </Interactive.Container>
         </Interactive.Stateless>
       ))}
@@ -168,7 +165,7 @@ export const WidthFull: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border widthVariant="full">
-          <span className="interactive-foreground">Full width container</span>
+          <span>Full width container</span>
         </Interactive.Container>
       </Interactive.Stateless>
     </div>
@@ -187,7 +184,7 @@ export const Rounding: StoryObj = {
           onClick={() => {}}
         >
           <Interactive.Container border roundingVariant={rounding}>
-            <span className="interactive-foreground">{rounding}</span>
+            <span>{rounding}</span>
           </Interactive.Container>
         </Interactive.Stateless>
       ))}
@@ -207,7 +204,7 @@ export const DisabledStory: StoryObj = {
           onClick={() => {}}
         >
           <Interactive.Container border>
-            <span className="interactive-foreground">Disabled</span>
+            <span>Disabled</span>
           </Interactive.Container>
         </Interactive.Stateless>
       </Disabled>
@@ -218,7 +215,7 @@ export const DisabledStory: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">Enabled</span>
+          <span>Enabled</span>
         </Interactive.Container>
       </Interactive.Stateless>
     </div>
@@ -236,7 +233,7 @@ export const Interaction: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">Forced hover</span>
+          <span>Forced hover</span>
         </Interactive.Container>
       </Interactive.Stateless>
 
@@ -247,7 +244,7 @@ export const Interaction: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">Forced active</span>
+          <span>Forced active</span>
         </Interactive.Container>
       </Interactive.Stateless>
 
@@ -257,7 +254,7 @@ export const Interaction: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">Normal (rest)</span>
+          <span>Normal (rest)</span>
         </Interactive.Container>
       </Interactive.Stateless>
     </div>
@@ -274,7 +271,7 @@ export const WithBorder: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">With border</span>
+          <span>With border</span>
         </Interactive.Container>
       </Interactive.Stateless>
 
@@ -284,7 +281,7 @@ export const WithBorder: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container>
-          <span className="interactive-foreground">Without border</span>
+          <span>Without border</span>
         </Interactive.Container>
       </Interactive.Stateless>
     </div>
@@ -296,7 +293,7 @@ export const AsLink: StoryObj = {
   render: () => (
     <Interactive.Stateless variant="action" href="/settings">
       <Interactive.Container border>
-        <span className="interactive-foreground">Go to Settings</span>
+        <span>Go to Settings</span>
       </Interactive.Container>
     </Interactive.Stateless>
   ),
@@ -312,7 +309,7 @@ export const SelectVariant: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">Selected (light)</span>
+          <span>Selected (light)</span>
         </Interactive.Container>
       </Interactive.Stateful>
 
@@ -322,7 +319,7 @@ export const SelectVariant: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">Unselected (light)</span>
+          <span>Unselected (light)</span>
         </Interactive.Container>
       </Interactive.Stateful>
 
@@ -332,7 +329,7 @@ export const SelectVariant: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">Selected (heavy)</span>
+          <span>Selected (heavy)</span>
         </Interactive.Container>
       </Interactive.Stateful>
 
@@ -342,7 +339,7 @@ export const SelectVariant: StoryObj = {
         onClick={() => {}}
       >
         <Interactive.Container border>
-          <span className="interactive-foreground">Unselected (heavy)</span>
+          <span>Unselected (heavy)</span>
         </Interactive.Container>
       </Interactive.Stateful>
     </div>

web/lib/opal/src/core/interactive/shared.css

@@ -21,9 +21,10 @@
   --interactive-easing: ease-in-out;
 }
 
-/* Base interactive surface */
+/* Base interactive surface — sets color directly so all descendants inherit. */
 .interactive {
   @apply cursor-pointer select-none;
+  color: var(--interactive-foreground);
   transition:
     background-color var(--interactive-duration) var(--interactive-easing),
     --interactive-foreground var(--interactive-duration)
@@ -43,14 +44,8 @@
   @apply border;
 }
 
-/* Utility classes — descendants opt in to parent-controlled foreground color.
-   No transition here — the parent interpolates the variables directly. */
-.interactive-foreground {
-  color: var(--interactive-foreground);
-}
-
-/* Icon foreground — reads from --interactive-foreground-icon, which defaults
-   to --interactive-foreground via the variant CSS rules. */
+/* Icon foreground — reads from --interactive-foreground-icon, which may differ
+   from --interactive-foreground (e.g. muted icons beside normal text). */
 .interactive-foreground-icon {
   color: var(--interactive-foreground-icon);
 }

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

@@ -0,0 +1,100 @@
+import React from "react";
+import { Slot } from "@radix-ui/react-slot";
+import { cn } from "@opal/utils";
+import { useDisabled } from "@opal/core/disabled/components";
+
+// ---------------------------------------------------------------------------
+// Types
+// ---------------------------------------------------------------------------
+
+interface InteractiveSimpleProps
+  extends Omit<
+    React.HTMLAttributes<HTMLElement>,
+    "className" | "style" | "color"
+  > {
+  ref?: React.Ref<HTMLElement>;
+
+  /**
+   * Tailwind group class (e.g. `"group/Card"`) for `group-hover:*` utilities.
+   */
+  group?: string;
+
+  /**
+   * URL to navigate to when clicked. Passed through Slot to the child.
+   */
+  href?: string;
+
+  /**
+   * Link target (e.g. `"_blank"`). Only used when `href` is provided.
+   */
+  target?: string;
+}
+
+// ---------------------------------------------------------------------------
+// InteractiveSimple
+// ---------------------------------------------------------------------------
+
+/**
+ * Minimal interactive surface primitive.
+ *
+ * Provides cursor styling, click handling, disabled integration, 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.
+ *
+ * Uses Radix `Slot` — merges props onto a single child element without
+ * adding any DOM node.
+ *
+ * @example
+ * ```tsx
+ * <Interactive.Simple onClick={handleClick} group="group/Card">
+ *   <Card>...</Card>
+ * </Interactive.Simple>
+ * ```
+ */
+function InteractiveSimple({
+  ref,
+  group,
+  href,
+  target,
+  ...props
+}: InteractiveSimpleProps) {
+  const { isDisabled, allowClick } = useDisabled();
+
+  const classes = cn(
+    "cursor-pointer select-none",
+    isDisabled && "cursor-not-allowed",
+    !props.onClick && !href && "!cursor-default !select-auto",
+    group
+  );
+
+  const { onClick, ...slotProps } = props;
+
+  const linkAttrs = href
+    ? {
+        href: isDisabled ? undefined : href,
+        target,
+        rel: target === "_blank" ? "noopener noreferrer" : undefined,
+      }
+    : {};
+
+  return (
+    <Slot
+      ref={ref}
+      className={classes}
+      aria-disabled={isDisabled || undefined}
+      {...linkAttrs}
+      {...slotProps}
+      onClick={
+        isDisabled && !allowClick
+          ? href
+            ? (e: React.MouseEvent) => e.preventDefault()
+            : undefined
+          : onClick
+      }
+    />
+  );
+}
+
+export { InteractiveSimple, type InteractiveSimpleProps };

web/lib/opal/src/core/interactive/stateful/README.md

@@ -8,7 +8,7 @@ Stateful interactive surface primitive for elements that maintain a value state
 
 | Prop | Type | Default | Description |
 |------|------|---------|-------------|
-| `variant` | `"select-light" \| "select-heavy" \| "select-tinted" \| "select-filter" \| "sidebar"` | `"select-heavy"` | Color variant |
+| `variant` | `"select-light" \| "select-heavy" \| "select-card" \| "select-tinted" \| "select-filter" \| "sidebar-heavy" \| "sidebar-light"` | `"select-heavy"` | Color variant |
 | `state` | `"empty" \| "filled" \| "selected"` | `"empty"` | Current value state |
 | `interaction` | `"rest" \| "hover" \| "active"` | `"rest"` | JS-controlled interaction override |
 | `group` | `string` | — | Tailwind group class for `group-hover:*` |
@@ -16,6 +16,16 @@ Stateful interactive surface primitive for elements that maintain a value state
 | `href` | `string` | — | URL for link behavior |
 | `target` | `string` | — | Link target (e.g. `"_blank"`) |
 
+## Variants
+
+- **`select-light`** — Transparent selected background. For inline toggles.
+- **`select-heavy`** — Tinted selected background (`action-link-01`). For list rows, model pickers, buttons.
+- **`select-card`** — Like `select-heavy`, but the filled state gets a visible background (`background-tint-00`) with neutral foreground. Designed for larger surfaces (cards) where background carries more of the visual distinction than foreground color alone.
+- **`select-tinted`** — Like `select-heavy` but with a tinted rest background (`background-tint-01`).
+- **`select-filter`** — Like `select-tinted` for empty/filled; selected state uses inverted backgrounds and inverted text.
+- **`sidebar-heavy`** — Sidebar navigation: muted when unselected, bold when selected.
+- **`sidebar-light`** — Sidebar navigation: uniformly muted across all states.
+
 ## State attribute
 
 Uses `data-interactive-state` (not `data-state`) to avoid conflicts with Radix UI, which injects its own `data-state` on trigger elements.

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

@@ -13,9 +13,11 @@ import type { ButtonType, WithoutStyles } from "@opal/types";
 type InteractiveStatefulVariant =
   | "select-light"
   | "select-heavy"
+  | "select-card"
   | "select-tinted"
   | "select-filter"
-  | "sidebar";
+  | "sidebar-heavy"
+  | "sidebar-light";
 type InteractiveStatefulState = "empty" | "filled" | "selected";
 type InteractiveStatefulInteraction = "rest" | "hover" | "active";
 
@@ -31,9 +33,11 @@ interface InteractiveStatefulProps
    *
    * - `"select-light"` — transparent selected background (for inline toggles)
    * - `"select-heavy"` — tinted selected background (for list rows, model pickers)
+   * - `"select-card"` — like select-heavy but filled state has a visible background (for cards/larger surfaces)
    * - `"select-tinted"` — like select-heavy but with a tinted rest background
    * - `"select-filter"` — like select-tinted for empty/filled; selected state uses inverted tint backgrounds and inverted text (for filter buttons)
-   * - `"sidebar"` — for sidebar navigation items
+   * - `"sidebar-heavy"` — sidebar navigation items: muted when unselected (text-03/text-02), bold when selected (text-04/text-03)
+   * - `"sidebar-light"` — sidebar navigation items: uniformly muted across all states (text-02/text-02)
    *
    * @default "select-heavy"
    */

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

@@ -11,7 +11,7 @@
    Children read the variables with no independent transitions.
 
    State dimension: `data-interactive-state` = "empty" | "filled" | "selected"
-   Variant dimension: `data-interactive-variant` = "select-light" | "select-heavy" | "select-tinted" | "sidebar"
+   Variant dimension: `data-interactive-variant` = "select-light" | "select-heavy" | "select-card" | "select-tinted" | "select-filter" | "sidebar-heavy" | "sidebar-light"
 
    Interaction override: `data-interaction="hover"` and `data-interaction="active"`
    allow JS-controlled visual state overrides.
@@ -114,6 +114,108 @@
   --interactive-foreground-icon: var(--action-link-03);
 }
 
+/* ===========================================================================
+   Select-Card — like Select-Heavy but filled has a visible background.
+   Designed for larger surfaces (cards) where background carries more of
+   the visual distinction than foreground color alone.
+   =========================================================================== */
+
+/* ---------------------------------------------------------------------------
+   Select-Card — Empty
+   --------------------------------------------------------------------------- */
+.interactive[data-interactive-variant="select-card"][data-interactive-state="empty"] {
+  @apply bg-transparent;
+  --interactive-foreground: var(--text-04);
+  --interactive-foreground-icon: var(--text-03);
+}
+.interactive[data-interactive-variant="select-card"][data-interactive-state="empty"]:hover:not(
+    [data-disabled]
+  ),
+.interactive[data-interactive-variant="select-card"][data-interactive-state="empty"][data-interaction="hover"]:not(
+    [data-disabled]
+  ) {
+  @apply bg-background-tint-02;
+  --interactive-foreground-icon: var(--text-04);
+}
+.interactive[data-interactive-variant="select-card"][data-interactive-state="empty"]:active:not(
+    [data-disabled]
+  ),
+.interactive[data-interactive-variant="select-card"][data-interactive-state="empty"][data-interaction="active"]:not(
+    [data-disabled]
+  ) {
+  @apply bg-background-neutral-00;
+  --interactive-foreground: var(--text-05);
+  --interactive-foreground-icon: var(--text-05);
+}
+.interactive[data-interactive-variant="select-card"][data-interactive-state="empty"][data-disabled] {
+  @apply bg-transparent;
+  --interactive-foreground: var(--text-01);
+  --interactive-foreground-icon: var(--text-01);
+}
+
+/* ---------------------------------------------------------------------------
+   Select-Card — Filled (visible background, neutral foreground)
+   --------------------------------------------------------------------------- */
+.interactive[data-interactive-variant="select-card"][data-interactive-state="filled"] {
+  @apply bg-background-tint-00;
+  --interactive-foreground: var(--text-04);
+  --interactive-foreground-icon: var(--text-03);
+}
+.interactive[data-interactive-variant="select-card"][data-interactive-state="filled"]:hover:not(
+    [data-disabled]
+  ),
+.interactive[data-interactive-variant="select-card"][data-interactive-state="filled"][data-interaction="hover"]:not(
+    [data-disabled]
+  ) {
+  @apply bg-background-tint-02;
+  --interactive-foreground-icon: var(--text-04);
+}
+.interactive[data-interactive-variant="select-card"][data-interactive-state="filled"]:active:not(
+    [data-disabled]
+  ),
+.interactive[data-interactive-variant="select-card"][data-interactive-state="filled"][data-interaction="active"]:not(
+    [data-disabled]
+  ) {
+  @apply bg-background-tint-00;
+  --interactive-foreground: var(--text-05);
+  --interactive-foreground-icon: var(--text-05);
+}
+.interactive[data-interactive-variant="select-card"][data-interactive-state="filled"][data-disabled] {
+  @apply bg-transparent;
+  --interactive-foreground: var(--text-01);
+  --interactive-foreground-icon: var(--text-01);
+}
+
+/* ---------------------------------------------------------------------------
+   Select-Card — Selected
+   --------------------------------------------------------------------------- */
+.interactive[data-interactive-variant="select-card"][data-interactive-state="selected"] {
+  @apply bg-[var(--action-link-01)];
+  --interactive-foreground: var(--action-link-05);
+  --interactive-foreground-icon: var(--action-link-05);
+}
+.interactive[data-interactive-variant="select-card"][data-interactive-state="selected"]:hover:not(
+    [data-disabled]
+  ),
+.interactive[data-interactive-variant="select-card"][data-interactive-state="selected"][data-interaction="hover"]:not(
+    [data-disabled]
+  ) {
+  @apply bg-background-tint-02;
+}
+.interactive[data-interactive-variant="select-card"][data-interactive-state="selected"]:active:not(
+    [data-disabled]
+  ),
+.interactive[data-interactive-variant="select-card"][data-interactive-state="selected"][data-interaction="active"]:not(
+    [data-disabled]
+  ) {
+  @apply bg-background-tint-00;
+}
+.interactive[data-interactive-variant="select-card"][data-interactive-state="selected"][data-disabled] {
+  @apply bg-transparent;
+  --interactive-foreground: var(--action-link-03);
+  --interactive-foreground-icon: var(--action-link-03);
+}
+
 /* ===========================================================================
    Select-Light — identical to Select-Heavy except selected bg is transparent
    =========================================================================== */
@@ -392,49 +494,115 @@
 }
 
 /* ===========================================================================
-   Sidebar
+   Sidebar-Heavy
+
+   Not selected: muted (text-03 / icon text-02)
+   Selected: default (text-04 / icon text-03)
    =========================================================================== */
 
 /* ---------------------------------------------------------------------------
-   Sidebar — Empty
+   Sidebar-Heavy — Empty
    --------------------------------------------------------------------------- */
-.interactive[data-interactive-variant="sidebar"][data-interactive-state="empty"] {
+.interactive[data-interactive-variant="sidebar-heavy"][data-interactive-state="empty"] {
   @apply bg-transparent;
+  --interactive-foreground: var(--text-03);
+  --interactive-foreground-icon: var(--text-02);
 }
-.interactive[data-interactive-variant="sidebar"][data-interactive-state="empty"]:hover:not(
+.interactive[data-interactive-variant="sidebar-heavy"][data-interactive-state="empty"]:hover:not(
     [data-disabled]
   ),
-.interactive[data-interactive-variant="sidebar"][data-interactive-state="empty"][data-interaction="hover"]:not(
+.interactive[data-interactive-variant="sidebar-heavy"][data-interactive-state="empty"][data-interaction="hover"]:not(
     [data-disabled]
   ) {
   @apply bg-background-tint-03;
 }
 
 /* ---------------------------------------------------------------------------
-   Sidebar — Filled
+   Sidebar-Heavy — Filled
    --------------------------------------------------------------------------- */
-.interactive[data-interactive-variant="sidebar"][data-interactive-state="filled"] {
+.interactive[data-interactive-variant="sidebar-heavy"][data-interactive-state="filled"] {
   @apply bg-transparent;
+  --interactive-foreground: var(--text-03);
+  --interactive-foreground-icon: var(--text-02);
 }
-.interactive[data-interactive-variant="sidebar"][data-interactive-state="filled"]:hover:not(
+.interactive[data-interactive-variant="sidebar-heavy"][data-interactive-state="filled"]:hover:not(
     [data-disabled]
   ),
-.interactive[data-interactive-variant="sidebar"][data-interactive-state="filled"][data-interaction="hover"]:not(
+.interactive[data-interactive-variant="sidebar-heavy"][data-interactive-state="filled"][data-interaction="hover"]:not(
     [data-disabled]
   ) {
   @apply bg-background-tint-03;
 }
 
 /* ---------------------------------------------------------------------------
-   Sidebar — Selected
+   Sidebar-Heavy — Selected
    --------------------------------------------------------------------------- */
-.interactive[data-interactive-variant="sidebar"][data-interactive-state="selected"] {
+.interactive[data-interactive-variant="sidebar-heavy"][data-interactive-state="selected"] {
   @apply bg-background-tint-00;
+  --interactive-foreground: var(--text-04);
+  --interactive-foreground-icon: var(--text-03);
 }
-.interactive[data-interactive-variant="sidebar"][data-interactive-state="selected"]:hover:not(
+.interactive[data-interactive-variant="sidebar-heavy"][data-interactive-state="selected"]:hover:not(
     [data-disabled]
   ),
-.interactive[data-interactive-variant="sidebar"][data-interactive-state="selected"][data-interaction="hover"]:not(
+.interactive[data-interactive-variant="sidebar-heavy"][data-interactive-state="selected"][data-interaction="hover"]:not(
+    [data-disabled]
+  ) {
+  @apply bg-background-tint-03;
+}
+
+/* ===========================================================================
+   Sidebar-Light
+
+   All states: prominence="muted-2x" colors (text-02 / icon text-02)
+   =========================================================================== */
+
+/* ---------------------------------------------------------------------------
+   Sidebar-Light — Empty
+   --------------------------------------------------------------------------- */
+.interactive[data-interactive-variant="sidebar-light"][data-interactive-state="empty"] {
+  @apply bg-transparent;
+  --interactive-foreground: var(--text-02);
+  --interactive-foreground-icon: var(--text-02);
+}
+.interactive[data-interactive-variant="sidebar-light"][data-interactive-state="empty"]:hover:not(
+    [data-disabled]
+  ),
+.interactive[data-interactive-variant="sidebar-light"][data-interactive-state="empty"][data-interaction="hover"]:not(
+    [data-disabled]
+  ) {
+  @apply bg-background-tint-03;
+}
+
+/* ---------------------------------------------------------------------------
+   Sidebar-Light — Filled
+   --------------------------------------------------------------------------- */
+.interactive[data-interactive-variant="sidebar-light"][data-interactive-state="filled"] {
+  @apply bg-transparent;
+  --interactive-foreground: var(--text-02);
+  --interactive-foreground-icon: var(--text-02);
+}
+.interactive[data-interactive-variant="sidebar-light"][data-interactive-state="filled"]:hover:not(
+    [data-disabled]
+  ),
+.interactive[data-interactive-variant="sidebar-light"][data-interactive-state="filled"][data-interaction="hover"]:not(
+    [data-disabled]
+  ) {
+  @apply bg-background-tint-03;
+}
+
+/* ---------------------------------------------------------------------------
+   Sidebar-Light — Selected
+   --------------------------------------------------------------------------- */
+.interactive[data-interactive-variant="sidebar-light"][data-interactive-state="selected"] {
+  @apply bg-background-tint-00;
+  --interactive-foreground: var(--text-02);
+  --interactive-foreground-icon: var(--text-02);
+}
+.interactive[data-interactive-variant="sidebar-light"][data-interactive-state="selected"]:hover:not(
+    [data-disabled]
+  ),
+.interactive[data-interactive-variant="sidebar-light"][data-interactive-state="selected"][data-interaction="hover"]:not(
     [data-disabled]
   ) {
   @apply bg-background-tint-03;

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

@@ -10,7 +10,7 @@ import type { ButtonType, WithoutStyles } from "@opal/types";
 // Types
 // ---------------------------------------------------------------------------
 
-type InteractiveStatelessVariant = "none" | "default" | "action" | "danger";
+type InteractiveStatelessVariant = "default" | "action" | "danger";
 type InteractiveStatelessProminence =
   | "primary"
   | "secondary"
@@ -108,8 +108,8 @@ function InteractiveStateless({
   );
 
   const dataAttrs = {
-    "data-interactive-variant": variant !== "none" ? variant : undefined,
-    "data-interactive-prominence": variant !== "none" ? prominence : undefined,
+    "data-interactive-variant": variant,
+    "data-interactive-prominence": prominence,
     "data-interaction": interaction !== "rest" ? interaction : undefined,
     "data-disabled": isDisabled ? "true" : undefined,
     "aria-disabled": isDisabled || undefined,

web/lib/opal/src/layouts/cards/header-layout/CardHeaderLayout.stories.tsx

@@ -0,0 +1,158 @@
+import type { Meta, StoryObj } from "@storybook/react";
+import { CardHeaderLayout } from "@opal/layouts";
+import { Button } from "@opal/components";
+import {
+  SvgArrowExchange,
+  SvgCheckSquare,
+  SvgGlobe,
+  SvgSettings,
+  SvgUnplug,
+} from "@opal/icons";
+import * as TooltipPrimitive from "@radix-ui/react-tooltip";
+import type { Decorator } from "@storybook/react";
+
+const withTooltipProvider: Decorator = (Story) => (
+  <TooltipPrimitive.Provider>
+    <Story />
+  </TooltipPrimitive.Provider>
+);
+
+const meta = {
+  title: "Layouts/CardHeaderLayout",
+  component: CardHeaderLayout,
+  tags: ["autodocs"],
+  decorators: [withTooltipProvider],
+  parameters: {
+    layout: "centered",
+  },
+} satisfies Meta<typeof CardHeaderLayout>;
+
+export default meta;
+
+type Story = StoryObj<typeof meta>;
+
+// ---------------------------------------------------------------------------
+// Stories
+// ---------------------------------------------------------------------------
+
+export const Default: Story = {
+  render: () => (
+    <div className="w-[28rem] border rounded-16">
+      <CardHeaderLayout
+        sizePreset="main-ui"
+        variant="section"
+        icon={SvgGlobe}
+        title="Google Search"
+        description="Web search provider"
+        rightChildren={
+          <Button prominence="tertiary" rightIcon={SvgArrowExchange}>
+            Connect
+          </Button>
+        }
+      />
+    </div>
+  ),
+};
+
+export const WithBothSlots: Story = {
+  render: () => (
+    <div className="w-[28rem] border rounded-16">
+      <CardHeaderLayout
+        sizePreset="main-ui"
+        variant="section"
+        icon={SvgGlobe}
+        title="Google Search"
+        description="Currently the default provider."
+        rightChildren={
+          <Button variant="action" prominence="tertiary" icon={SvgCheckSquare}>
+            Current Default
+          </Button>
+        }
+        bottomRightChildren={
+          <>
+            <Button
+              icon={SvgUnplug}
+              tooltip="Disconnect"
+              prominence="tertiary"
+              size="sm"
+            />
+            <Button
+              icon={SvgSettings}
+              tooltip="Edit"
+              prominence="tertiary"
+              size="sm"
+            />
+          </>
+        }
+      />
+    </div>
+  ),
+};
+
+export const RightChildrenOnly: Story = {
+  render: () => (
+    <div className="w-[28rem] border rounded-16">
+      <CardHeaderLayout
+        sizePreset="main-ui"
+        variant="section"
+        icon={SvgGlobe}
+        title="OpenAI"
+        description="Not configured"
+        rightChildren={
+          <Button prominence="tertiary" rightIcon={SvgArrowExchange}>
+            Connect
+          </Button>
+        }
+      />
+    </div>
+  ),
+};
+
+export const NoRightChildren: Story = {
+  render: () => (
+    <div className="w-[28rem] border rounded-16">
+      <CardHeaderLayout
+        sizePreset="main-ui"
+        variant="section"
+        icon={SvgGlobe}
+        title="Section Header"
+        description="No actions on the right."
+      />
+    </div>
+  ),
+};
+
+export const LongContent: Story = {
+  render: () => (
+    <div className="w-[28rem] border rounded-16">
+      <CardHeaderLayout
+        sizePreset="main-ui"
+        variant="section"
+        icon={SvgGlobe}
+        title="Very Long Provider Name That Should Truncate"
+        description="This is a much longer description that tests how the layout handles overflow when the content area needs to shrink."
+        rightChildren={
+          <Button variant="action" prominence="tertiary" icon={SvgCheckSquare}>
+            Current Default
+          </Button>
+        }
+        bottomRightChildren={
+          <>
+            <Button
+              icon={SvgUnplug}
+              prominence="tertiary"
+              size="sm"
+              tooltip="Disconnect"
+            />
+            <Button
+              icon={SvgSettings}
+              prominence="tertiary"
+              size="sm"
+              tooltip="Edit"
+            />
+          </>
+        }
+      />
+    </div>
+  ),
+};

web/lib/opal/src/layouts/cards/header-layout/README.md

@@ -0,0 +1,94 @@
+# CardHeaderLayout
+
+**Import:** `import { CardHeaderLayout, type CardHeaderLayoutProps } from "@opal/layouts";`
+
+A card header layout that pairs a [`Content`](../../content/README.md) block with a right-side column of vertically stacked children.
+
+## Why CardHeaderLayout?
+
+[`ContentAction`](../../content-action/README.md) provides a single `rightChildren` slot. Card headers typically need two distinct right-side regions — a primary action on top and secondary actions on the bottom. `CardHeaderLayout` provides this with `rightChildren` and `bottomRightChildren` slots, with no padding or gap between them so the caller has full control over spacing.
+
+## Props
+
+Inherits **all** props from [`Content`](../../content/README.md) (icon, title, description, sizePreset, variant, etc.) plus:
+
+| Prop | Type | Default | Description |
+|---|---|---|---|
+| `rightChildren` | `ReactNode` | `undefined` | Content rendered to the right of the Content block (top of right column). |
+| `bottomRightChildren` | `ReactNode` | `undefined` | Content rendered below `rightChildren` in the same column. Laid out as `flex flex-row`. |
+
+## Layout Structure
+
+```
+┌──────────────────────────────────────────────────────┐
+│ [Content (p-2, self-start)]  [rightChildren]         │
+│  icon + title + description  [bottomRightChildren]   │
+└──────────────────────────────────────────────────────┘
+```
+
+- Outer wrapper: `flex flex-row items-stretch w-full`
+- Content area: `flex-1 min-w-0 self-start p-2` — top-aligned with fixed padding
+- Right column: `flex flex-col items-end justify-between shrink-0` — no padding, no gap
+- `bottomRightChildren` wrapper: `flex flex-row` — lays children out horizontally
+
+The right column uses `justify-between` so when both slots are present, `rightChildren` sits at the top and `bottomRightChildren` at the bottom.
+
+## Usage
+
+### Card with primary and secondary actions
+
+```tsx
+import { CardHeaderLayout } from "@opal/layouts";
+import { Button } from "@opal/components";
+import { SvgGlobe, SvgSettings, SvgUnplug, SvgCheckSquare } from "@opal/icons";
+
+<CardHeaderLayout
+  icon={SvgGlobe}
+  title="Google Search"
+  description="Web search provider"
+  sizePreset="main-ui"
+  variant="section"
+  rightChildren={
+    <Button icon={SvgCheckSquare} variant="action" prominence="tertiary">
+      Current Default
+    </Button>
+  }
+  bottomRightChildren={
+    <>
+      <Button icon={SvgUnplug} size="sm" prominence="tertiary" tooltip="Disconnect" />
+      <Button icon={SvgSettings} size="sm" prominence="tertiary" tooltip="Edit" />
+    </>
+  }
+/>
+```
+
+### Card with only a connect action
+
+```tsx
+<CardHeaderLayout
+  icon={SvgCloud}
+  title="OpenAI"
+  description="Not configured"
+  sizePreset="main-ui"
+  variant="section"
+  rightChildren={
+    <Button rightIcon={SvgArrowExchange} prominence="tertiary">
+      Connect
+    </Button>
+  }
+/>
+```
+
+### No right children
+
+```tsx
+<CardHeaderLayout
+  icon={SvgInfo}
+  title="Section Header"
+  description="Description text"
+  sizePreset="main-content"
+  variant="section"
+/>
+```
+
+When both `rightChildren` and `bottomRightChildren` are omitted, the component renders only the padded `Content`.

web/lib/opal/src/layouts/cards/header-layout/components.tsx

@@ -0,0 +1,73 @@
+import { Content, type ContentProps } from "@opal/layouts/content/components";
+
+// ---------------------------------------------------------------------------
+// Types
+// ---------------------------------------------------------------------------
+
+type CardHeaderLayoutProps = ContentProps & {
+  /** Content rendered to the right of the Content block. */
+  rightChildren?: React.ReactNode;
+
+  /** Content rendered below `rightChildren` in the same column. */
+  bottomRightChildren?: React.ReactNode;
+};
+
+// ---------------------------------------------------------------------------
+// CardHeaderLayout
+// ---------------------------------------------------------------------------
+
+/**
+ * A card header layout that pairs a {@link Content} block (with `p-2`)
+ * with a right-side column.
+ *
+ * The right column contains two vertically stacked slots —
+ * `rightChildren` on top, `bottomRightChildren` below — with no
+ * padding or gap between them.
+ *
+ * @example
+ * ```tsx
+ * <CardHeaderLayout
+ *   icon={SvgGlobe}
+ *   title="Google"
+ *   description="Search engine"
+ *   sizePreset="main-ui"
+ *   variant="section"
+ *   rightChildren={<Button>Connect</Button>}
+ *   bottomRightChildren={
+ *     <>
+ *       <Button icon={SvgUnplug} size="sm" prominence="tertiary" />
+ *       <Button icon={SvgSettings} size="sm" prominence="tertiary" />
+ *     </>
+ *   }
+ * />
+ * ```
+ */
+function CardHeaderLayout({
+  rightChildren,
+  bottomRightChildren,
+  ...contentProps
+}: CardHeaderLayoutProps) {
+  const hasRight = rightChildren || bottomRightChildren;
+
+  return (
+    <div className="flex flex-row items-stretch w-full">
+      <div className="flex-1 min-w-0 self-start p-2">
+        <Content {...contentProps} />
+      </div>
+      {hasRight && (
+        <div className="flex flex-col items-end shrink-0">
+          {rightChildren && <div className="flex-1">{rightChildren}</div>}
+          {bottomRightChildren && (
+            <div className="flex flex-row">{bottomRightChildren}</div>
+          )}
+        </div>
+      )}
+    </div>
+  );
+}
+
+// ---------------------------------------------------------------------------
+// Exports
+// ---------------------------------------------------------------------------
+
+export { CardHeaderLayout, type CardHeaderLayoutProps };

web/lib/opal/src/layouts/content/ContentLg.tsx

@@ -4,10 +4,8 @@ import { Button } from "@opal/components/buttons/button/components";
 import type { ContainerSizeVariants } from "@opal/types";
 import SvgEdit from "@opal/icons/edit";
 import type { IconFunctionComponent, RichStr } from "@opal/types";
-import {
-  resolveStr,
-  toPlainString,
-} from "@opal/components/text/InlineMarkdown";
+import { Text, type TextFont } from "@opal/components/text/components";
+import { toPlainString } from "@opal/components/text/InlineMarkdown";
 import { cn } from "@opal/utils";
 import { useState } from "react";
 
@@ -24,8 +22,8 @@ interface ContentLgPresetConfig {
   iconContainerPadding: string;
   /** Gap between icon container and content (CSS value). */
   gap: string;
-  /** Tailwind font class for the title. */
-  titleFont: string;
+  /** Opal font name for the title (without `font-` prefix). */
+  titleFont: TextFont;
   /** Title line-height — also used as icon container min-height (CSS value). */
   lineHeight: string;
   /** Button `size` prop for the edit button. Uses the shared `SizeVariant` scale. */
@@ -53,9 +51,6 @@ interface ContentLgProps {
   /** Size preset. Default: `"headline"`. */
   sizePreset?: ContentLgSizePreset;
 
-  /** When `true`, the title color hooks into `Interactive`'s `--interactive-foreground` variable. */
-  withInteractive?: boolean;
-
   /** Ref forwarded to the root `<div>`. */
   ref?: React.Ref<HTMLDivElement>;
 }
@@ -69,7 +64,7 @@ const CONTENT_LG_PRESETS: Record<ContentLgSizePreset, ContentLgPresetConfig> = {
     iconSize: "2rem",
     iconContainerPadding: "p-0.5",
     gap: "0.25rem",
-    titleFont: "font-heading-h2",
+    titleFont: "heading-h2",
     lineHeight: "2.25rem",
     editButtonSize: "md",
     editButtonPadding: "p-1",
@@ -78,7 +73,7 @@ const CONTENT_LG_PRESETS: Record<ContentLgSizePreset, ContentLgPresetConfig> = {
     iconSize: "1.25rem",
     iconContainerPadding: "p-1",
     gap: "0rem",
-    titleFont: "font-heading-h3-muted",
+    titleFont: "heading-h3-muted",
     lineHeight: "1.75rem",
     editButtonSize: "sm",
     editButtonPadding: "p-0.5",
@@ -96,7 +91,6 @@ function ContentLg({
   description,
   editable,
   onTitleChange,
-  withInteractive,
   ref,
 }: ContentLgProps) {
   const [editing, setEditing] = useState(false);
@@ -116,12 +110,7 @@ function ContentLg({
   }
 
   return (
-    <div
-      ref={ref}
-      className="opal-content-lg"
-      data-interactive={withInteractive || undefined}
-      style={{ gap: config.gap }}
-    >
+    <div ref={ref} className="opal-content-lg" style={{ gap: config.gap }}>
       {Icon && (
         <div
           className={cn(
@@ -142,14 +131,17 @@ function ContentLg({
           {editing ? (
             <div className="opal-content-lg-input-sizer">
               <span
-                className={cn("opal-content-lg-input-mirror", config.titleFont)}
+                className={cn(
+                  "opal-content-lg-input-mirror",
+                  `font-${config.titleFont}`
+                )}
               >
                 {editValue || "\u00A0"}
               </span>
               <input
                 className={cn(
                   "opal-content-lg-input",
-                  config.titleFont,
+                  `font-${config.titleFont}`,
                   "text-text-04"
                 )}
                 value={editValue}
@@ -169,19 +161,15 @@ function ContentLg({
               />
             </div>
           ) : (
-            <span
-              className={cn(
-                "opal-content-lg-title",
-                config.titleFont,
-                "text-text-04",
-                editable && "cursor-pointer"
-              )}
-              onClick={editable ? startEditing : undefined}
-              style={{ height: config.lineHeight }}
+            <Text
+              font={config.titleFont}
+              color="inherit"
+              maxLines={1}
               title={toPlainString(title)}
+              onClick={editable ? startEditing : undefined}
             >
-              {resolveStr(title)}
-            </span>
+              {title}
+            </Text>
           )}
 
           {editable && !editing && (
@@ -204,8 +192,10 @@ function ContentLg({
         </div>
 
         {description && toPlainString(description) && (
-          <div className="opal-content-lg-description font-secondary-body text-text-03">
-            {resolveStr(description)}
+          <div className="opal-content-lg-description">
+            <Text font="secondary-body" color="text-03" as="p">
+              {description}
+            </Text>
           </div>
         )}
       </div>