diff --git a/src/routers/messages.py b/src/routers/messages.py
index 3acdc1e5..ef2e3068 100644
--- a/src/routers/messages.py
+++ b/src/routers/messages.py
@@ -18,7 +18,7 @@ from sqlalchemy.orm.attributes import flag_modified
 
 from src import crud, schemas
 from src.config import settings
-from src.dependencies import db
+from src.dependencies import db, tracked_db
 from src.deriver import enqueue
 from src.exceptions import FileTooLargeError, ResourceNotFoundException
 from src.security import require_auth
@@ -141,7 +141,6 @@ async def create_messages_with_file(
     session_id: str = Path(...),
     form_data: schemas.MessageUploadCreate = Depends(parse_upload_form),
     file: UploadFile = File(...),
-    db: AsyncSession = db,
 ):
     """Create messages from uploaded files. Files are converted to text and split into multiple messages."""
 
@@ -160,22 +159,23 @@ async def create_messages_with_file(
         created_at=form_data.created_at,
     )
 
-    # Create messages
-    message_creates = [item["message_create"] for item in all_message_data]
-    created_messages = await crud.create_messages(
-        db,
-        messages=message_creates,
-        workspace_name=workspace_id,
-        session_name=session_id,
-    )
+    async with tracked_db("messages.upload") as db:
+        # Create messages
+        message_creates = [item["message_create"] for item in all_message_data]
+        created_messages = await crud.create_messages(
+            db,
+            messages=message_creates,
+            workspace_name=workspace_id,
+            session_name=session_id,
+        )
 
-    # Update internal_metadata for file-related messages
-    for i, message in enumerate(created_messages):
-        file_metadata = all_message_data[i]["file_metadata"]
-        message.internal_metadata.update(file_metadata)
-        flag_modified(message, "internal_metadata")
+        # Update internal_metadata for file-related messages
+        for i, message in enumerate(created_messages):
+            file_metadata = all_message_data[i]["file_metadata"]
+            message.internal_metadata.update(file_metadata)
+            flag_modified(message, "internal_metadata")
 
-    await db.commit()
+        await db.commit()
 
     # Enqueue for processing (same as regular messages)
     payloads = [
diff --git a/tests/conftest.py b/tests/conftest.py
index 3c9b8e63..d03a989b 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -787,6 +787,7 @@ def mock_tracked_db(request: pytest.FixtureRequest):
         patch("src.deriver.queue_manager.tracked_db", mock_tracked_db_context),
         patch("src.deriver.consumer.tracked_db", mock_tracked_db_context),
         patch("src.deriver.enqueue.tracked_db", mock_tracked_db_context),
+        patch("src.routers.messages.tracked_db", mock_tracked_db_context),
         patch("src.routers.peers.tracked_db", mock_tracked_db_context),
         patch("src.crud.representation.tracked_db", mock_tracked_db_context),
         patch("src.dreamer.orchestrator.tracked_db", mock_tracked_db_context),
diff --git a/tests/routes/test_files.py b/tests/routes/test_files.py
index 3af9f60b..097a744c 100644
--- a/tests/routes/test_files.py
+++ b/tests/routes/test_files.py
@@ -1,6 +1,7 @@
 # File upload tests for session endpoints
 import io
 import json
+from contextlib import asynccontextmanager
 from typing import Any
 
 import pytest
@@ -9,9 +10,12 @@ from nanoid import generate as generate_nanoid
 from sqlalchemy import select
 from sqlalchemy.ext.asyncio import AsyncSession
 
-from src import models
+from src import models, schemas
 from src.config import settings
+from src.dependencies import get_db
+from src.main import app
 from src.models import Peer, Workspace
+from src.routers import messages as messages_router
 
 
 async def _create_test_session(
@@ -161,6 +165,65 @@ async def test_create_messages_with_empty_json_file(
     assert data[0]["session_id"] == session_name
 
 
+@pytest.mark.asyncio
+async def test_file_upload_extracts_before_opening_db_session(
+    client: TestClient,
+    db_session: AsyncSession,
+    sample_data: tuple[Workspace, Peer],
+    monkeypatch: pytest.MonkeyPatch,
+):
+    """File extraction can perform remote OCR, so DB work must start after it."""
+    test_workspace, test_peer = sample_data
+    test_session = await _create_test_session(db_session, test_workspace)
+    events: list[str] = []
+
+    async def fake_process_file_uploads_for_messages(*_args: Any, **_kwargs: Any):
+        events.append("extract")
+        return [
+            {
+                "message_create": schemas.MessageCreate(
+                    content="extracted text",
+                    peer_id=test_peer.name,
+                ),
+                "file_metadata": {
+                    "file_id": "test-file",
+                    "filename": "test.txt",
+                    "chunk_index": 0,
+                    "total_chunks": 1,
+                    "original_file_size": 13,
+                    "content_type": "text/plain",
+                    "chunk_character_range": [0, 13],
+                },
+            }
+        ]
+
+    async def override_get_db():
+        events.append("db_open")
+        yield db_session
+
+    @asynccontextmanager
+    async def fake_tracked_db(_: str | None = None):
+        events.append("db_open")
+        yield db_session
+
+    monkeypatch.setattr(
+        messages_router,
+        "process_file_uploads_for_messages",
+        fake_process_file_uploads_for_messages,
+    )
+    monkeypatch.setattr(messages_router, "tracked_db", fake_tracked_db, raising=False)
+    monkeypatch.setitem(app.dependency_overrides, get_db, override_get_db)
+
+    response = client.post(
+        _get_upload_url(test_workspace.name, test_session.name),
+        files={"file": ("test.txt", io.BytesIO(b"test content"), "text/plain")},
+        data={"peer_id": test_peer.name},
+    )
+
+    assert response.status_code == 201
+    assert events == ["extract", "db_open"]
+
+
 @pytest.mark.asyncio
 async def test_create_messages_with_unsupported_file_type(
     client: TestClient,