diff --git a/litellm/proxy/guardrails/guardrail_hooks/ovalix/ovalix.py b/litellm/proxy/guardrails/guardrail_hooks/ovalix/ovalix.py
index d24a12ed7e8..8d7b7e1b81c 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/ovalix/ovalix.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/ovalix/ovalix.py
@@ -289,6 +289,7 @@ class OvalixGuardrail(CustomGuardrail):
         actor: str,
         session_id: str,
         target: CheckpointTarget,
+        oversize: bool = False,
     ) -> Mapping[str, object]:
         """Call the Ovalix Tracker checkpoint API and return the JSON response.
 
@@ -313,6 +314,7 @@ class OvalixGuardrail(CustomGuardrail):
             "data": data,
             "tool": "LiteLLM",
             **routing,
+            **(MappingProxyType({"oversize": True}) if oversize else _NO_METADATA),
         }
         response: Final = await self._async_handler.post(
             f"{self._tracker_api_base}/tracking/beta/{route}", headers=self._tracker_headers, json=payload
@@ -332,9 +334,12 @@ class OvalixGuardrail(CustomGuardrail):
         session_id: str,
         target: CheckpointTarget,
         escalation_reason: str,
+        oversize: bool = False,
     ) -> str | None:
         try:
-            resp: Final = await self._call_checkpoint(data_type, data, checkpoint_id, actor, session_id, target)
+            resp: Final = await self._call_checkpoint(
+                data_type, data, checkpoint_id, actor, session_id, target, oversize=oversize
+            )
         except Exception as e:
             verbose_proxy_logger.exception("Ovalix checkpoint call failed: %s", e)
             raise GuardrailRaisedException(
@@ -377,7 +382,14 @@ class OvalixGuardrail(CustomGuardrail):
         for part in sorted(file_parts, key=lambda p: p.message_index, reverse=True):
             data = await self._file_part_to_data(part)
             reason = await self._block_reason_for_item(
-                "FILE", data, checkpoint_id, actor, session_id, target, _FILE_BLOCK_ESCALATION_REASON
+                "FILE",
+                data,
+                checkpoint_id,
+                actor,
+                session_id,
+                target,
+                _FILE_BLOCK_ESCALATION_REASON,
+                oversize=part.oversize,
             )
             if reason is not None:
                 return reason
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_ovalix.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_ovalix.py
index 5b39ed42ed1..2b6d3ac91b1 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_ovalix.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_ovalix.py
@@ -21,6 +21,7 @@ from litellm.proxy.guardrails.guardrail_hooks.ovalix.ovalix import (
     OvalixGuardrailMissingSecrets,
     ResolvedRouting,
 )
+from litellm.proxy.guardrails.guardrail_hooks.ovalix.ovalix_extraction import FilePart
 from litellm.types.guardrails import GuardrailEventHooks
 from litellm.types.utils import GenericGuardrailAPIInputs
 
@@ -994,6 +995,26 @@ async def test_file_checkpoint_call_routes_to_litellm_file_endpoint():
     assert seen["url"] == "https://t/tracking/beta/file_checkpoint"
 
 
+@pytest.mark.asyncio
+@pytest.mark.parametrize("oversize", [True, False])
+async def test_file_checkpoint_flags_oversize_parts(oversize):
+    g = _static_guardrail()
+    part = FilePart(name="huge.bin", data=None, mime_hint=None, inline=oversize, oversize=oversize, message_index=0)
+    seen = {}
+
+    async def _post(url, headers=None, json=None):
+        seen["last"] = json
+        r = MagicMock()
+        r.json.return_value = _ALLOW
+        r.raise_for_status = MagicMock()
+        return r
+
+    with patch.object(g._async_handler, "post", new=_post):
+        await g._check_files_for_block([part], "file-1", "a", "s", CheckpointTarget("app-1", "request"))
+    assert seen["last"]["data"]["content"] is None
+    assert seen["last"].get("oversize", False) is oversize
+
+
 @pytest.mark.asyncio
 async def test_tool_call_block_raises():
     g = _static_guardrail()