diff --git a/litellm/proxy/openai_files_endpoints/batch_guardrails.py b/litellm/proxy/openai_files_endpoints/batch_guardrails.py
index 78aa04c2e65..5c886ca0e9b 100644
--- a/litellm/proxy/openai_files_endpoints/batch_guardrails.py
+++ b/litellm/proxy/openai_files_endpoints/batch_guardrails.py
@@ -539,6 +539,9 @@ def rewrite_batch_input_file(file_source: BinaryIO, result: BatchScanResult) ->
             line = text.rstrip("\n") if change is None else _read_spooled(result.redactions, change)
             output.write((("\n" if wrote_any else "") + line).encode("utf-8"))
             wrote_any = True
+    except BaseException:
+        output.close()
+        raise
     finally:
         file_source.seek(0)
     output.seek(0)
diff --git a/litellm/proxy/openai_files_endpoints/files_endpoints.py b/litellm/proxy/openai_files_endpoints/files_endpoints.py
index 92f176f2f4f..37cfd9d073d 100644
--- a/litellm/proxy/openai_files_endpoints/files_endpoints.py
+++ b/litellm/proxy/openai_files_endpoints/files_endpoints.py
@@ -535,13 +535,13 @@ async def create_file(
             )
 
         # Prepare the file data according to FileTypes
+        if scan_result is not None:
+            spools.append(scan_result.redactions)
         upload_source: Final = (
             await asyncio.to_thread(rewrite_batch_input_file, file_source, scan_result)
             if scan_result is not None and scan_result.changes
             else file_source
         )
-        if scan_result is not None:
-            spools.append(scan_result.redactions)
         if upload_source is not file_source:
             spools.append(upload_source)
         file_data: Final = (file.filename, upload_source, file.content_type)
diff --git a/tests/test_litellm/proxy/openai_files_endpoint/test_batch_guardrails.py b/tests/test_litellm/proxy/openai_files_endpoint/test_batch_guardrails.py
index 0e07249f7a7..a05b8ae530c 100644
--- a/tests/test_litellm/proxy/openai_files_endpoint/test_batch_guardrails.py
+++ b/tests/test_litellm/proxy/openai_files_endpoint/test_batch_guardrails.py
@@ -758,6 +758,38 @@ async def test_the_scan_spool_is_closed_when_the_upload_is_refused():
     assert spools and all(handle.closed for handle in spools)
 
 
+@pytest.mark.asyncio
+async def test_the_rewrite_closes_its_own_output_when_it_cannot_finish():
+    """A half-written rewrite spool has no owner yet, so it has to clean up after itself."""
+    import litellm.proxy.openai_files_endpoints.batch_guardrails as bg
+
+    source = _jsonl(_record("a"), _record("b", content="my secret is here"))
+    result = await _scan_full(source, FakeProxyLogging(_redact_containing("secret")))
+
+    spools = []
+    real = bg.tempfile.SpooledTemporaryFile
+
+    def _tracking(*args, **kwargs):
+        handle = real(*args, **kwargs)
+        spools.append(handle)
+        return handle
+
+    def _boom(*args, **kwargs):
+        raise OSError("no space left on device")
+
+    bg.tempfile.SpooledTemporaryFile = _tracking
+    original_read = bg._read_spooled
+    bg._read_spooled = _boom
+    try:
+        with pytest.raises(OSError):
+            rewrite_batch_input_file(source, result)
+    finally:
+        bg.tempfile.SpooledTemporaryFile = real
+        bg._read_spooled = original_read
+
+    assert spools and all(handle.closed for handle in spools)
+
+
 @pytest.mark.asyncio
 async def test_the_scan_spool_is_closed_when_a_record_escapes_the_iterator():
     """A raise from inside the read loop bypasses the per-record outcome path entirely."""