diff --git a/backend/api/cloud.py b/backend/api/cloud.py
index 6046291..f995099 100644
--- a/backend/api/cloud.py
+++ b/backend/api/cloud.py
@@ -339,23 +339,28 @@ async def oauth_initiate(
             detail=f"Unsupported OAuth provider: {provider}. Valid providers: {sorted(VALID_OAUTH_PROVIDERS)}",
         )
 
-    state_token = secrets.token_urlsafe(32)
-    redis_client = request.app.state.redis
-    await redis_client.setex(f"oauth_state:{state_token}", 1800, str(current_user.id))
-
-    redirect_uri = f"{settings.backend_url}/api/cloud/oauth/callback/{provider}"
-
+    # Pre-flight: validate credentials are configured before allocating Redis state
     if provider == "google_drive" and (not settings.google_client_id or not settings.google_client_secret):
         raise HTTPException(
             status_code=status.HTTP_400_BAD_REQUEST,
             detail="Google Drive OAuth is not configured on this server. Set GOOGLE_CLIENT_ID and GOOGLE_CLIENT_SECRET in your environment.",
         )
-    if provider == "onedrive" and (not settings.onedrive_client_id or not settings.onedrive_client_secret):
+    if provider == "onedrive" and (
+        not settings.onedrive_client_id
+        or not settings.onedrive_client_secret
+        or not settings.onedrive_tenant_id
+    ):
         raise HTTPException(
             status_code=status.HTTP_400_BAD_REQUEST,
             detail="OneDrive OAuth is not configured on this server. Set ONEDRIVE_CLIENT_ID, ONEDRIVE_CLIENT_SECRET, and ONEDRIVE_TENANT_ID in your environment.",
         )
 
+    state_token = secrets.token_urlsafe(32)
+    redis_client = request.app.state.redis
+    await redis_client.setex(f"oauth_state:{state_token}", 1800, str(current_user.id))
+
+    redirect_uri = f"{settings.backend_url}/api/cloud/oauth/callback/{provider}"
+
     if provider == "google_drive":
         from google_auth_oauthlib.flow import Flow  # lazy import
 
diff --git a/backend/api/documents.py b/backend/api/documents.py
index fe28580..d7d271c 100644
--- a/backend/api/documents.py
+++ b/backend/api/documents.py
@@ -756,6 +756,8 @@ async def stream_document_content(
             status_code=503,
             detail="Cloud connection requires re-authentication. Please reconnect in Settings.",
         ) from exc
+    except HTTPException:
+        raise
     except Exception as exc:
         raise HTTPException(
             status_code=502,
diff --git a/backend/tests/test_cloud.py b/backend/tests/test_cloud.py
index 6321a40..55ce2af 100644
--- a/backend/tests/test_cloud.py
+++ b/backend/tests/test_cloud.py
@@ -784,7 +784,8 @@ async def test_oauth_initiate_returns_json_url(async_client, db_session, monkeyp
 async def test_oauth_initiate_google_drive_not_configured(async_client, db_session, monkeypatch):
     """GET /api/cloud/oauth/initiate/google_drive returns 400 with env-var hint when creds missing.
 
-    Pre-flight check (plan 05-12): empty GOOGLE_CLIENT_ID/SECRET → 400 before touching OAuth libs.
+    Pre-flight check (plan 05-12): empty GOOGLE_CLIENT_ID/SECRET → 400 BEFORE Redis state write.
+    Asserts Redis store is empty to confirm no orphan state tokens are created on misconfigured calls.
     """
     from main import app
     from config import settings
@@ -802,16 +803,19 @@ async def test_oauth_initiate_google_drive_not_configured(async_client, db_sessi
         follow_redirects=False,
     )
 
+    redis_keys = list(fake_redis._store.keys())
     app.state.redis = None
 
     assert resp.status_code == 400, f"Expected 400, got {resp.status_code}: {resp.text}"
     assert "GOOGLE_CLIENT_ID" in resp.json()["detail"], f"Unexpected detail: {resp.json()['detail']}"
+    assert len(redis_keys) == 0, f"Expected no Redis state token written on pre-flight failure, got: {redis_keys}"
 
 
 async def test_oauth_initiate_onedrive_not_configured(async_client, db_session, monkeypatch):
     """GET /api/cloud/oauth/initiate/onedrive returns 400 with env-var hint when creds missing.
 
-    Pre-flight check (plan 05-12): empty ONEDRIVE_CLIENT_ID → 400 before touching MSAL.
+    Pre-flight check (plan 05-12): empty ONEDRIVE_CLIENT_ID → 400 BEFORE Redis state write.
+    Asserts Redis store is empty to confirm no orphan state tokens are created on misconfigured calls.
     """
     from main import app
     from config import settings
@@ -829,10 +833,12 @@ async def test_oauth_initiate_onedrive_not_configured(async_client, db_session,
         follow_redirects=False,
     )
 
+    redis_keys = list(fake_redis._store.keys())
     app.state.redis = None
 
     assert resp.status_code == 400, f"Expected 400, got {resp.status_code}: {resp.text}"
     assert "ONEDRIVE_CLIENT_ID" in resp.json()["detail"], f"Unexpected detail: {resp.json()['detail']}"
+    assert len(redis_keys) == 0, f"Expected no Redis state token written on pre-flight failure, got: {redis_keys}"
 
 
 async def test_oauth_initiate_requires_auth(async_client, db_session):
diff --git a/docker-compose.yml b/docker-compose.yml
index 9034b77..f1ef398 100644
--- a/docker-compose.yml
+++ b/docker-compose.yml
@@ -87,6 +87,7 @@ services:
       - MINIO_SECRET_KEY=${MINIO_SECRET_KEY}
       - MINIO_BUCKET=${MINIO_BUCKET}
       - REDIS_URL=${REDIS_URL}
+      - CLOUD_CREDS_KEY=${CLOUD_CREDS_KEY}
       - PYTHONDONTWRITEBYTECODE=1
     volumes:
       - ./backend:/app