diff --git a/surfsense_backend/tests/e2e/test_document_upload.py b/surfsense_backend/tests/e2e/test_document_upload.py
index f3ff8b7a6..c1193a63b 100644
--- a/surfsense_backend/tests/e2e/test_document_upload.py
+++ b/surfsense_backend/tests/e2e/test_document_upload.py
@@ -353,16 +353,16 @@ class TestDuplicateContentDetection:
         assert resp2.status_code == 200
         second_ids = resp2.json()["document_ids"]
         cleanup_doc_ids.extend(second_ids)
+        assert second_ids, (
+            "Expected at least one document id for renamed duplicate content upload"
+        )
 
-        if second_ids:
-            statuses = await poll_document_status(
-                client, headers, second_ids, search_space_id=search_space_id
-            )
-            for did in second_ids:
-                assert statuses[did]["status"]["state"] == "failed"
-                assert "duplicate" in (
-                    statuses[did]["status"].get("reason", "").lower()
-                )
+        statuses = await poll_document_status(
+            client, headers, second_ids, search_space_id=search_space_id
+        )
+        for did in second_ids:
+            assert statuses[did]["status"]["state"] == "failed"
+            assert "duplicate" in statuses[did]["status"].get("reason", "").lower()
 
 
 # ---------------------------------------------------------------------------
@@ -387,16 +387,16 @@ class TestEmptyFileUpload:
 
         doc_ids = resp.json()["document_ids"]
         cleanup_doc_ids.extend(doc_ids)
+        assert doc_ids, "Expected at least one document id for empty PDF upload"
 
-        if doc_ids:
-            statuses = await poll_document_status(
-                client, headers, doc_ids, search_space_id=search_space_id, timeout=120.0
+        statuses = await poll_document_status(
+            client, headers, doc_ids, search_space_id=search_space_id, timeout=120.0
+        )
+        for did in doc_ids:
+            assert statuses[did]["status"]["state"] == "failed"
+            assert statuses[did]["status"].get("reason"), (
+                "Failed document should include a reason"
             )
-            for did in doc_ids:
-                assert statuses[did]["status"]["state"] == "failed"
-                assert statuses[did]["status"].get("reason"), (
-                    "Failed document should include a reason"
-                )
 
 
 # ---------------------------------------------------------------------------
diff --git a/surfsense_backend/tests/utils/helpers.py b/surfsense_backend/tests/utils/helpers.py
index ad58d5141..270db7125 100644
--- a/surfsense_backend/tests/utils/helpers.py
+++ b/surfsense_backend/tests/utils/helpers.py
@@ -124,20 +124,31 @@ async def poll_document_status(
     terminal state (``ready`` or ``failed``) or *timeout* seconds elapse.
 
     Returns a mapping of ``{document_id: status_item_dict}``.
+
+    Retries on transient transport errors until timeout.
     """
     ids_param = ",".join(str(d) for d in document_ids)
     terminal_states = {"ready", "failed"}
     elapsed = 0.0
+    items: dict[int, dict] = {}
+    last_transport_error: Exception | None = None
 
     while elapsed < timeout:
-        resp = await client.get(
-            "/api/v1/documents/status",
-            headers=headers,
-            params={
-                "search_space_id": search_space_id,
-                "document_ids": ids_param,
-            },
-        )
+        try:
+            resp = await client.get(
+                "/api/v1/documents/status",
+                headers=headers,
+                params={
+                    "search_space_id": search_space_id,
+                    "document_ids": ids_param,
+                },
+            )
+        except (httpx.ReadError, httpx.ConnectError, httpx.TimeoutException) as exc:
+            last_transport_error = exc
+            await asyncio.sleep(interval)
+            elapsed += interval
+            continue
+
         assert resp.status_code == 200, (
             f"Status poll failed ({resp.status_code}): {resp.text}"
         )
@@ -154,7 +165,8 @@ async def poll_document_status(
 
     raise TimeoutError(
         f"Documents {document_ids} did not reach terminal state within {timeout}s. "
-        f"Last status: {items}"
+        f"Last status: {items}. "
+        f"Last transport error: {last_transport_error!r}"
     )