diff --git a/litellm/proxy/guardrails/guardrail_hooks/agent_365/agent_365.py b/litellm/proxy/guardrails/guardrail_hooks/agent_365/agent_365.py
index cb6ff9a5355..40264d111d7 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/agent_365/agent_365.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/agent_365/agent_365.py
@@ -60,6 +60,10 @@ GATEWAY_SCOPE_TEMPLATE: Final = "api://{client_id}/access_as_user"
 _GATEWAY_OWNED_TOKEN_ERRORS: Final = frozenset(
     {"invalid_client", "unauthorized_client", "invalid_scope", "invalid_resource"}
 )
+# Entra reports a malformed or unverifiable assertion as ``invalid_client`` too; only its AADSTS50027xx
+# (InvalidJwtToken) sub-codes tell that apart from a bad gateway secret.
+_INVALID_ASSERTION_AADSTS_PREFIX: Final = "50027"
+_AADSTS_CODES_ADAPTER: Final = TypeAdapter(tuple[int, ...])
 _MCP_CALL_TYPES: Final[tuple[str, ...]] = ("mcp_call", "call_mcp_tool")
 _TOOL_INPUT_SCHEMA_ADAPTER: Final = TypeAdapter(dict[str, object])
 _OBO_CACHE_MAX_ENTRIES: Final = 1000
@@ -76,6 +80,13 @@ def _parse_expires_in(raw: object) -> float:
         return _DEFAULT_TOKEN_TTL_SECONDS
 
 
+def _parse_aadsts_codes(raw: object) -> tuple[int, ...]:
+    try:
+        return _AADSTS_CODES_ADAPTER.validate_python(raw)
+    except ValidationError:
+        return ()
+
+
 def _parse_tool_input_schema(raw: object) -> Mapping[str, object] | None:
     try:
         return _TOOL_INPUT_SCHEMA_ADAPTER.validate_python(raw)
@@ -117,11 +128,20 @@ class _BlockedDetail(TypedDict):
 
 
 class Agent365TokenExchangeError(Exception):
-    def __init__(self, status_code: int, error_code: str, description: str) -> None:
+    def __init__(self, status_code: int, error_code: str, description: str, aadsts_codes: tuple[int, ...] = ()) -> None:
         super().__init__(f"{error_code}: {description}")
         self.status_code = status_code
         self.error_code = error_code
         self.description = description
+        self.aadsts_codes = aadsts_codes
+
+    @property
+    def gateway_owned(self) -> bool:
+        """Whether the gateway's own client credentials, scope or resource were refused, as opposed to the
+        caller's assertion. The caller cannot fix a gateway-owned rejection by signing in again."""
+        if self.error_code not in _GATEWAY_OWNED_TOKEN_ERRORS:
+            return False
+        return not any(str(code).startswith(_INVALID_ASSERTION_AADSTS_PREFIX) for code in self.aadsts_codes)
 
 
 class Agent365MalformedResponseError(Exception):
@@ -219,7 +239,7 @@ class Agent365Guardrail(CustomGuardrail):
         try:
             obo_token: Final = await self._get_obo_token(assertion)
         except Agent365TokenExchangeError as exc:
-            if exc.error_code in _GATEWAY_OWNED_TOKEN_ERRORS:
+            if exc.gateway_owned:
                 return self._handle_unavailable(
                     data=data,
                     tool_name=tool_name,
@@ -446,7 +466,7 @@ class Agent365Guardrail(CustomGuardrail):
         try:
             await self._get_obo_token(assertion)
         except Agent365TokenExchangeError as exc:
-            return exc.error_code not in _GATEWAY_OWNED_TOKEN_ERRORS
+            return not exc.gateway_owned
         except (Agent365ThrottledError, Agent365MalformedResponseError, httpx.HTTPError, LitellmTimeout, TimeoutError):
             return False
         return False
@@ -492,6 +512,7 @@ class Agent365Guardrail(CustomGuardrail):
                 status_code=response.status_code,
                 error_code=str(body.get("error", "invalid_grant")),
                 description=str(body.get("error_description", ""))[:512],
+                aadsts_codes=_parse_aadsts_codes(body.get("error_codes")),
             )
         if "access_token" not in body:
             raise Agent365MalformedResponseError("the Entra token endpoint returned no access_token")
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server.py
index 511433837c0..aaa472a2400 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server.py
@@ -9066,13 +9066,24 @@ class TestAgent365ChallengeAtConnect:
         assert await self._connect(self._server([self.GATEWAY_SCOPE]), self.ENTRA_BEARER) is None
 
     @pytest.mark.asyncio
-    async def test_assertion_entra_refuses_to_exchange_is_challenged(self, agent_365_guardrail):
+    @pytest.mark.parametrize(
+        "entra_body",
+        [
+            {"error": "invalid_grant", "error_description": "AADSTS700084: The refresh token was issued..."},
+            {
+                "error": "invalid_client",
+                "error_description": "AADSTS5002723: Invalid JWT token.",
+                "error_codes": [5002723],
+            },
+        ],
+        ids=["expired-or-wrong-audience", "forged-reported-as-invalid_client"],
+    )
+    async def test_assertion_entra_refuses_to_exchange_is_challenged(self, agent_365_guardrail, entra_body):
         """An expired, wrong-audience, or forged Entra token looks like a valid one. Only the OBO exchange
         can tell, and its verdict must arrive at connect, where WWW-Authenticate reaches the client,
-        rather than inside every tools/call JSON-RPC error."""
-        agent_365_guardrail.async_handler.post.return_value = self._entra_response(
-            400, {"error": "invalid_grant", "error_description": "AADSTS700084: The refresh token was issued..."}
-        )
+        rather than inside every tools/call JSON-RPC error. Entra files a forged assertion under
+        ``invalid_client`` with an AADSTS50027xx sub-code, which must not read as a gateway secret problem."""
+        agent_365_guardrail.async_handler.post.return_value = self._entra_response(400, entra_body)
 
         challenge = await self._connect(self._server([self.GATEWAY_SCOPE]), self.ENTRA_BEARER)
 
@@ -9088,7 +9099,16 @@ class TestAgent365ChallengeAtConnect:
     @pytest.mark.parametrize(
         "entra_outcome",
         [
-            {"return_value": _entra_response(401, {"error": "invalid_client"})},
+            {
+                "return_value": _entra_response(
+                    401,
+                    {
+                        "error": "invalid_client",
+                        "error_description": "AADSTS7000215: Invalid client secret",
+                        "error_codes": [7000215],
+                    },
+                )
+            },
             {"return_value": _entra_response(503, {"error": "temporarily_unavailable"})},
             {"side_effect": httpx.ConnectError("dns")},
         ],
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_agent_365.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_agent_365.py
index 6466bd4549d..ba9253cb415 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_agent_365.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_agent_365.py
@@ -631,6 +631,30 @@ class TestUnreachableFallback:
         assert error_code in info["guardrail_response"]["reason"]
         assert "client_secret" in info["guardrail_response"]["reason"]
 
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("aadsts_code", [5002710, 5002723], ids=["malformed-header", "no-kid"])
+    async def test_malformed_assertion_reported_as_invalid_client_is_a_caller_401(self, aadsts_code: int):
+        """Entra answers ``invalid_client`` for a forged or garbled assertion (AADSTS50027xx) exactly as for a
+        bad gateway secret; the sub-code is what says the caller, not the gateway, has to fix it."""
+        handler: Final = FakeHandler(
+            [
+                _response(
+                    401,
+                    {
+                        "error": "invalid_client",
+                        "error_description": f"AADSTS{aadsts_code}: Invalid JWT token.",
+                        "error_codes": [aadsts_code],
+                    },
+                )
+            ]
+        )
+        guardrail: Final = _make_guardrail(handler)
+        data: Final = _mcp_data()
+        with pytest.raises(HTTPException) as exc_info:
+            await _run(guardrail, data)
+        assert exc_info.value.status_code == 401
+        assert "client_secret" not in _guardrail_info(data)["guardrail_response"]["reason"]
+
     @pytest.mark.asyncio
     async def test_gateway_credential_rejection_follows_fail_open(self):
         handler: Final = FakeHandler(