diff --git a/tests/e2e/batches/batch_cleanup.py b/tests/e2e/batches/batch_cleanup.py
index 86e47c0b1e1a..5b3baaa624c2 100644
--- a/tests/e2e/batches/batch_cleanup.py
+++ b/tests/e2e/batches/batch_cleanup.py
@@ -1,3 +1,4 @@
+import warnings
 from builtins import ExceptionGroup
 from collections.abc import Callable
 from itertools import count
@@ -12,8 +13,9 @@
 CLEANUP_DELAYS: Final = (1.0, 2.0, 4.0)
 BATCH_TERMINAL_STATUSES: Final = frozenset({"completed", "failed", "expired", "cancelled"})
 BATCH_PENDING_STATUSES: Final = frozenset({"validating", "in_progress", "finalizing", "cancelling"})
-BATCH_CANCEL_TIMEOUT_SECONDS: Final = 660.0
+BATCH_CANCEL_TIMEOUT_SECONDS: Final = 120.0
 BATCH_CANCEL_POLL_SECONDS: Final = 10.0
+FILE_IN_USE_REFUSAL: Final = "batch(es) in non-terminal state"
 
 
 class BatchCleanupClient(Protocol):
@@ -26,6 +28,10 @@ def retrieve_batch(self, batch_id: str, *, key: str, provider: str | None = None
     def cancel_batch(self, batch_id: str, *, key: str, provider: str | None = None) -> Result[BatchObject]: ...
 
 
+class BatchCleanupLeftover(UserWarning):
+    pass
+
+
 def cleanup_result[R: BaseModel](
     action: Callable[[], Result[R]], *, wait: Callable[[float], None] = sleep
 ) -> Result[R]:
@@ -59,6 +65,13 @@ def cleanup_file(client: BatchCleanupClient, file_id: str, *, key: str, provider
     result: Final = cleanup_result(delete)
     if isinstance(result, UnknownApiError) and result.status_code == 404:
         return
+    if isinstance(result, UnknownApiError) and result.status_code == 400 and FILE_IN_USE_REFUSAL in result.body:
+        warnings.warn(
+            f"Left file {file_id} in place: LiteLLM refused to delete it while a batch still references it",
+            BatchCleanupLeftover,
+            stacklevel=2,
+        )
+        return
     deleted: Final = _require_cleanup_success(result, f"Delete file {file_id}")
     assert deleted.deleted is True or (
         deleted.deleted is None and is_managed_id(file_id) and deleted.id == file_id and deleted.object == "file"
@@ -120,9 +133,17 @@ def cleanup_batch(
         )
         if current.status == "cancelling" and not needs_terminal_state:
             return
-        assert clock() < deadline, (
-            f"Batch {batch_id} cancellation did not finish within {BATCH_CANCEL_TIMEOUT_SECONDS}s"
-        )
+        if clock() >= deadline:
+            assert current.status == "cancelling", (
+                f"Batch {batch_id} cancellation did not finish within {BATCH_CANCEL_TIMEOUT_SECONDS}s, "
+                f"last status {current.status}"
+            )
+            warnings.warn(
+                f"Left batch {batch_id} cancelling after {BATCH_CANCEL_TIMEOUT_SECONDS}s for the provider to finish",
+                BatchCleanupLeftover,
+                stacklevel=2,
+            )
+            return
         wait(BATCH_CANCEL_POLL_SECONDS)
 
 
diff --git a/tests/e2e/batches/test_batch_cleanup.py b/tests/e2e/batches/test_batch_cleanup.py
index a0932a80dfe0..5e2ac12d3005 100644
--- a/tests/e2e/batches/test_batch_cleanup.py
+++ b/tests/e2e/batches/test_batch_cleanup.py
@@ -4,7 +4,14 @@
 from unittest.mock import Mock, call
 
 import pytest
-from batch_cleanup import BATCH_CANCEL_TIMEOUT_SECONDS, CLEANUP_DELAYS, cleanup_batch, cleanup_file, cleanup_result
+from batch_cleanup import (
+    BATCH_CANCEL_TIMEOUT_SECONDS,
+    CLEANUP_DELAYS,
+    BatchCleanupLeftover,
+    cleanup_batch,
+    cleanup_file,
+    cleanup_result,
+)
 from batch_client import AZURE_FILE_EXPIRY_SECONDS, BatchObject, FileDeleteResponse, batch_upload_form
 from capabilities import CAPABILITIES, Capability
 from e2e_http import NetworkError, RateLimitedError, Result, Success, UnknownApiError
@@ -13,6 +20,10 @@
 
 MANAGED_FILE_ID: Final = "bGl0ZWxsbV9wcm94eTtmaWxlLTE="
 MANAGED_BATCH_ID: Final = "bGl0ZWxsbV9wcm94eTtiYXRjaC0x"
+IN_USE_REFUSAL: Final = (
+    f'{{"error":{{"message":"Cannot delete file {MANAGED_FILE_ID}. The file is referenced by 1 batch(es) in '
+    f'non-terminal state: {MANAGED_BATCH_ID}: cancelling. ","type":"invalid_request_error","code":"400"}}}}'
+)
 
 
 class ExpectedCalls[T]:
@@ -125,6 +136,29 @@ def test_success_response_must_confirm_deletion(self) -> None:
             cleanup_file(client, "file-1", key="test-key")
         client.calls.assert_done()
 
+    def test_delete_refused_because_a_batch_still_references_the_file_is_left_and_reported(self) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls((f"delete None {MANAGED_FILE_ID}",)),
+            files=(UnknownApiError(status_code=400, body=IN_USE_REFUSAL),),
+        )
+        with pytest.warns(BatchCleanupLeftover, match=MANAGED_FILE_ID):
+            cleanup_file(client, MANAGED_FILE_ID, key="test-key")
+        client.calls.assert_done()
+
+    @pytest.mark.parametrize(
+        "failure",
+        [
+            UnknownApiError(status_code=400, body="Invalid file id"),
+            UnknownApiError(status_code=409, body=IN_USE_REFUSAL),
+            UnknownApiError(status_code=501, body=IN_USE_REFUSAL),
+        ],
+    )
+    def test_any_other_delete_failure_still_raises(self, failure: UnknownApiError) -> None:
+        client: Final = CleanupClient(calls=ExpectedCalls((f"delete None {MANAGED_FILE_ID}",)), files=(failure,))
+        with pytest.raises(AssertionError, match=f"Delete file {MANAGED_FILE_ID} failed: HTTP {failure.status_code}"):
+            cleanup_file(client, MANAGED_FILE_ID, key="test-key")
+        client.calls.assert_done()
+
     def test_cleanup_is_idempotent_when_file_is_already_deleted(self) -> None:
         client: Final = CleanupClient(
             calls=ExpectedCalls(("delete azure file-1",)),
@@ -188,28 +222,50 @@ def test_cancelling_batch_is_polled_until_terminal_without_cancelling_again(self
         client.calls.assert_done()
         delays.assert_done()
 
-    def test_cancellation_timeout_is_reported_but_file_and_key_cleanup_still_run(self) -> None:
+    def test_batch_still_cancelling_at_the_deadline_and_its_input_file_are_left_and_reported(self) -> None:
         client: Final = CleanupClient(
             calls=ExpectedCalls(
                 (
                     f"retrieve None {MANAGED_BATCH_ID}",
                     f"retrieve None {MANAGED_BATCH_ID}",
-                    "delete None file-1",
+                    f"delete None {MANAGED_FILE_ID}",
                     "delete key test-key",
                 )
             ),
             batches=(batch("cancelling"), batch("cancelling")),
-            files=(deleted_file(),),
+            files=(UnknownApiError(status_code=400, body=IN_USE_REFUSAL),),
         )
         times: Final = (0.0, BATCH_CANCEL_TIMEOUT_SECONDS)
         ticks: Final[Callable[[], float]] = Mock(side_effect=times)
         manager: Final = ResourceManager(client=client, strict_cleanup=True)
         key: Final = manager.key()
-        manager.defer(lambda: cleanup_file(client, "file-1", key=key))
+        manager.defer(lambda: cleanup_file(client, MANAGED_FILE_ID, key=key))
         manager.defer(lambda: cleanup_batch(client, MANAGED_BATCH_ID, key=key, clock=ticks))
-        with pytest.raises(ExceptionGroup) as caught:
+        with pytest.warns(BatchCleanupLeftover) as leftovers:
             manager.teardown()
-        assert "cancellation did not finish" in str(caught.value.exceptions[0])
+        client.calls.assert_done()
+        messages: Final = tuple(str(warning.message) for warning in leftovers)
+        assert len(messages) == 2
+        assert MANAGED_BATCH_ID in messages[0] and "cancelling" in messages[0]
+        assert MANAGED_FILE_ID in messages[1]
+
+    @pytest.mark.parametrize(
+        "last, reported",
+        [
+            (batch("in_progress"), f"did not finish within {BATCH_CANCEL_TIMEOUT_SECONDS}s, last status in_progress"),
+            (UnknownApiError(status_code=403, body="forbidden"), "after cancellation failed: HTTP 403"),
+        ],
+    )
+    def test_anything_but_still_cancelling_at_the_deadline_still_fails(
+        self, last: Result[BatchObject], reported: str
+    ) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls((f"retrieve None {MANAGED_BATCH_ID}",) * 2), batches=(batch("cancelling"), last)
+        )
+        times: Final = (0.0, BATCH_CANCEL_TIMEOUT_SECONDS)
+        ticks: Final[Callable[[], float]] = Mock(side_effect=times)
+        with pytest.raises(AssertionError, match=reported):
+            cleanup_batch(client, MANAGED_BATCH_ID, key="test-key", clock=ticks)
         client.calls.assert_done()
 
     @pytest.mark.parametrize("status", ["completed", "failed", "expired", "cancelled"])
diff --git a/tests/e2e/batches/test_batches_e2e.py b/tests/e2e/batches/test_batches_e2e.py
index 191f3b4be208..44c5417d7858 100644
--- a/tests/e2e/batches/test_batches_e2e.py
+++ b/tests/e2e/batches/test_batches_e2e.py
@@ -93,11 +93,11 @@ class _GovCloudBedrockRecord(BaseModel):
     model_input: _GovCloudBedrockInput = Field(alias="modelInput")
 
 
-# Azure / Vertex cancel and the pre-cancel re-retrieve are provider-side flakes
+# Vertex cancel and the pre-cancel re-retrieve are provider-side flakes
 # (connection refused, brief 500s) and the registry only has one basic cell per
 # provider (shared across scenarios). Create + retrieve already prove routing;
-# cancel is still deferred for cleanup, just not asserted for these two.
-_CANCEL_ASSERTED_PROVIDERS = frozenset({"openai", "bedrock"})
+# cancel is still deferred for cleanup, just not asserted for Vertex.
+_CANCEL_ASSERTED_PROVIDERS = frozenset({"openai", "azure", "bedrock"})
 
 
 def _transient_status(status_code: int) -> bool:
diff --git a/tests/e2e/ui/tests/mcp/mcpTools.spec.ts b/tests/e2e/ui/tests/mcp/mcpTools.spec.ts
index 225ca8b94491..3f0833ca7415 100644
--- a/tests/e2e/ui/tests/mcp/mcpTools.spec.ts
+++ b/tests/e2e/ui/tests/mcp/mcpTools.spec.ts
@@ -42,7 +42,7 @@ test.describe("MCP Tools", () => {
 
     // Non-empty would still pass if the proxy returned some other server's tools.
     await expect(toolCard(toolList, TOOL_NAME)).toBeVisible();
-    await expect(toolCard(toolList, "ask_question")).toBeVisible();
+    await expect(toolCard(toolList, "ask_wiki_question")).toBeVisible();
     await expect(toolCard(toolList, "read_wiki_contents")).toBeVisible();
 
     // No other tool's name or description contains this string, so exactly one card survives.