diff --git a/src/api/connectors.py b/src/api/connectors.py
index 665962d87..61ef852ad 100644
--- a/src/api/connectors.py
+++ b/src/api/connectors.py
@@ -185,7 +185,7 @@ async def compute_orphans_for_connector_type(
     for conn in active:
         try:
             connector = await connector_service.get_connector(conn.connection_id)
-            if not connector or not connector.is_authenticated:
+            if not connector:
                 logger.info(
                     "Skipping orphan compute — connection unauthenticated",
                     connector_type=connector_type,
@@ -193,6 +193,17 @@ async def compute_orphans_for_connector_type(
                 )
                 return None
 
+            # Always re-authenticate before making API calls so that stale
+            # cached access tokens (Google tokens last 1 hour) are refreshed.
+            # This mirrors the pattern used in connector_sync.
+            if not await connector.authenticate():
+                logger.info(
+                    "Skipping orphan compute — re-authentication failed",
+                    connector_type=connector_type,
+                    connection_id=conn.connection_id,
+                )
+                return None
+
             # Drive the per-id existence check via cfg.file_ids when the
             # connector supports it (SharePoint / OneDrive / Google Drive).
             # The flat default of list_files() only returns the *root* listing
@@ -235,6 +246,7 @@ async def compute_orphans_for_connector_type(
                 connector_type=connector_type,
                 connection_id=conn.connection_id,
                 error=str(e),
+                error_type=type(e).__name__,
             )
             return None
 
diff --git a/src/connectors/google_drive/oauth.py b/src/connectors/google_drive/oauth.py
index 1d1e88bb2..53c5645e8 100644
--- a/src/connectors/google_drive/oauth.py
+++ b/src/connectors/google_drive/oauth.py
@@ -129,7 +129,15 @@ async def load_credentials(self) -> Credentials | None:
             except Exception as e:
                 logger.debug("[GoogleDrive] load_credentials: token refresh failed: %s", e)
                 self.creds = None
-                self._remove_token_file()
+                # Only wipe the token file for permanent failures (revoked or
+                # invalid grant). Transient failures (network timeout, etc.)
+                # should not force the user through re-authentication.
+                error_str = str(e).lower()
+                is_permanent = any(
+                    k in error_str for k in ("invalid_grant", "revoked", "unauthorized_client")
+                )
+                if is_permanent:
+                    self._remove_token_file()
                 raise ValueError(
                     f"Failed to refresh Google Drive credentials. "
                     f"The refresh token may have expired or been revoked. "
diff --git a/tests/unit/api/test_reconcile_orphans_for_connector_type.py b/tests/unit/api/test_reconcile_orphans_for_connector_type.py
index 9e339ca37..8ffac1095 100644
--- a/tests/unit/api/test_reconcile_orphans_for_connector_type.py
+++ b/tests/unit/api/test_reconcile_orphans_for_connector_type.py
@@ -30,6 +30,7 @@ def _make_connection(connection_id: str, is_active: bool = True):
 def _make_connector(remote_file_ids, *, authenticated=True, raise_on_list=False):
     connector = MagicMock()
     connector.is_authenticated = authenticated
+    connector.authenticate = AsyncMock(return_value=authenticated)
     if raise_on_list:
         connector.list_files = AsyncMock(side_effect=RuntimeError("graph 503"))
     else:
@@ -315,6 +316,7 @@ async def test_paginated_listing_aggregates_all_pages():
     conn = _make_connection("c1")
     connector = MagicMock()
     connector.is_authenticated = True
+    connector.authenticate = AsyncMock(return_value=True)
     pages = [
         {"files": [{"id": "a"}], "nextPageToken": "tok-1"},
         {"files": [{"id": "b"}, {"id": "c"}]},