diff --git a/tests/e2e/batches/COVERAGE.md b/tests/e2e/batches/COVERAGE.md
index 69ba9d781ec..f95ea1f2649 100644
--- a/tests/e2e/batches/COVERAGE.md
+++ b/tests/e2e/batches/COVERAGE.md
@@ -139,6 +139,9 @@ fallback for interrupted runs: immediate deletion remains the normal cleanup.
 Azure's minimum supported native expiry is 14 days, so a three-day expiry cannot
 be requested through its Files API
 
+The Azure entry in `files_settings` must use `api_version: 2025-04-01-preview`
+for raw uploads to honor expiry, matching the batch deployment's API version
+
 ## Terminal state + cost write-back (cross-run marker baton)
 
 The 24h completion window rules out submit-and-wait inside one run, so
diff --git a/tests/e2e/batches/batch_cleanup.py b/tests/e2e/batches/batch_cleanup.py
index dd79c776758..3fd6802f696 100644
--- a/tests/e2e/batches/batch_cleanup.py
+++ b/tests/e2e/batches/batch_cleanup.py
@@ -51,7 +51,9 @@ def cleanup_file(client: BatchCleanupClient, file_id: str, *, key: str, provider
     if isinstance(result, UnknownApiError) and result.status_code == 404:
         return
     deleted: Final = _require_cleanup_success(result, f"Delete file {file_id}")
-    assert deleted.deleted, f"Delete file {file_id} did not confirm deletion"
+    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"
+    ), f"Delete file {file_id} did not confirm deletion"
 
 
 def cleanup_batch(
diff --git a/tests/e2e/batches/batch_client.py b/tests/e2e/batches/batch_client.py
index 84a902b0b11..c9c77e1f12e 100644
--- a/tests/e2e/batches/batch_client.py
+++ b/tests/e2e/batches/batch_client.py
@@ -99,7 +99,7 @@ class BatchList(BaseModel):
 class FileDeleteResponse(BaseModel):
     id: str
     object: str | None = None
-    deleted: bool
+    deleted: bool | None = None
 
 
 class BatchCreateBody(BaseModel):
diff --git a/tests/e2e/batches/test_batch_cleanup.py b/tests/e2e/batches/test_batch_cleanup.py
index 9715370d9b7..15dead6d36d 100644
--- a/tests/e2e/batches/test_batch_cleanup.py
+++ b/tests/e2e/batches/test_batch_cleanup.py
@@ -12,6 +12,7 @@ from e2e_http import NetworkError, RateLimitedError, Result, Success, UnknownApi
 from lifecycle import ResourceManager
 from models import KeyGenerateBody
 
+MANAGED_FILE_ID: Final = "bGl0ZWxsbV9wcm94eTtmaWxlLTE="
 MANAGED_BATCH_ID: Final = "bGl0ZWxsbV9wcm94eTtiYXRjaC0x"
 
 
@@ -53,6 +54,20 @@ def deleted_file(*, deleted: bool = True) -> Success[FileDeleteResponse]:
 
 
 class TestFileCleanup:
+    def test_managed_delete_accepts_the_deleted_file_object(self) -> None:
+        response: Final = Success(
+            status_code=200, data=FileDeleteResponse.model_validate({"id": MANAGED_FILE_ID, "object": "file"})
+        )
+        client: Final = CleanupClient(files=iter((response,)))
+        cleanup_file(client, MANAGED_FILE_ID, key="test-key")
+        assert client.calls == [f"delete None {MANAGED_FILE_ID}"]
+
+    @pytest.mark.parametrize("file_id", ["file-1", MANAGED_FILE_ID])
+    def test_a_success_status_without_a_deletion_confirmation_is_rejected(self, file_id: str) -> None:
+        client: Final = CleanupClient(files=iter((Success(status_code=200, data=FileDeleteResponse(id=file_id)),)))
+        with pytest.raises(AssertionError, match="did not confirm deletion"):
+            cleanup_file(client, file_id, key="test-key")
+
     @pytest.mark.parametrize("cap", CAPABILITIES, ids=[cap.id for cap in CAPABILITIES])
     def test_deletes_raw_files_through_the_upload_provider(self, cap: Capability) -> None:
         client: Final = CleanupClient(files=iter((deleted_file(),)))