diff --git a/tests/test_litellm/llms/custom_httpx/test_llm_http_handler.py b/tests/test_litellm/llms/custom_httpx/test_llm_http_handler.py
index 177c71eeae7..fe093edd6f5 100644
--- a/tests/test_litellm/llms/custom_httpx/test_llm_http_handler.py
+++ b/tests/test_litellm/llms/custom_httpx/test_llm_http_handler.py
@@ -2757,3 +2757,175 @@ def test_video_generation_with_input_reference_keeps_file_multipart():
         "seconds": "4",
     }
     assert result.status == "queued"
+
+
+AZURE_AI_HOST = "myfoundry.services.ai.azure.com"
+AZURE_AI_BASE = f"https://{AZURE_AI_HOST}"
+
+TOOL_WITH_AN_UNSUPPORTED_FIELD = {
+    "type": "function",
+    "function": {"name": "lookup", "parameters": {"type": "object", "properties": {}}},
+    "strict": True,
+}
+
+A_COMPLETION = {
+    "id": "chatcmpl-1",
+    "object": "chat.completion",
+    "created": 1,
+    "model": "grok-3",
+    "choices": [
+        {"index": 0, "message": {"role": "assistant", "content": "sent"}, "finish_reason": "stop"}
+    ],
+    "usage": {"prompt_tokens": 1, "completion_tokens": 1, "total_tokens": 2},
+}
+
+TOOL_LEVEL_REJECTION = "Extra inputs are not permitted: tools[0].strict"
+UNRELATED_REJECTION = "Extra inputs are not permitted: temperature"
+A_REJECTION_THE_PROVIDER_CANNOT_FIX = "The model is not available in this region"
+
+
+class _RecordedAzureAI:
+    def __init__(self, responses: list[httpx.Response]) -> None:
+        self._responses = responses
+        self.bodies: list[dict] = []
+
+    def __call__(self, request: httpx.Request) -> httpx.Response:
+        self.bodies.append(json.loads(request.content))
+        return self._responses[min(len(self.bodies) - 1, len(self._responses) - 1)]
+
+
+@pytest.fixture
+def httpx_transport(monkeypatch):
+    monkeypatch.setattr(litellm, "disable_aiohttp_transport", True)
+
+
+def _rejection(message: str) -> httpx.Response:
+    return httpx.Response(422, json={"error": {"message": message}})
+
+
+def _call_azure_ai(recorder: _RecordedAzureAI, **overrides):
+    import respx
+
+    with respx.mock:
+        respx.route(host=AZURE_AI_HOST).mock(side_effect=recorder)
+        return litellm.completion(
+            model="azure_ai/grok-3",
+            messages=[{"role": "user", "content": "hi"}],
+            tools=[TOOL_WITH_AN_UNSUPPORTED_FIELD],
+            api_base=AZURE_AI_BASE,
+            api_key="fake-key",
+            **overrides,
+        )
+
+
+def test_a_tool_field_the_provider_rejects_is_dropped_and_the_call_retried():
+    recorder = _RecordedAzureAI(
+        [_rejection(TOOL_LEVEL_REJECTION), httpx.Response(200, json=A_COMPLETION)]
+    )
+
+    response = _call_azure_ai(recorder)
+
+    assert len(recorder.bodies) == 2
+    assert recorder.bodies[0]["tools"][0]["strict"] is True
+    assert "strict" not in recorder.bodies[1]["tools"][0]
+    assert response.choices[0].message.content == "sent"
+
+
+def test_the_retry_changes_only_the_field_the_provider_named():
+    recorder = _RecordedAzureAI(
+        [_rejection(TOOL_LEVEL_REJECTION), httpx.Response(200, json=A_COMPLETION)]
+    )
+
+    _call_azure_ai(recorder)
+
+    first, second = recorder.bodies
+    assert second["messages"] == first["messages"]
+    assert second["model"] == first["model"]
+    assert second["tools"][0]["function"] == first["tools"][0]["function"]
+
+
+def test_a_provider_that_keeps_rejecting_is_not_retried_forever():
+    recorder = _RecordedAzureAI([_rejection(TOOL_LEVEL_REJECTION)])
+
+    with pytest.raises(litellm.BadRequestError) as raised:
+        _call_azure_ai(recorder)
+
+    assert len(recorder.bodies) == 2
+    assert raised.value.status_code == 422
+
+
+def test_a_rejection_the_provider_cannot_fix_is_not_retried_at_all():
+    recorder = _RecordedAzureAI([_rejection(A_REJECTION_THE_PROVIDER_CANNOT_FIX)])
+
+    with pytest.raises(litellm.BadRequestError):
+        _call_azure_ai(recorder)
+
+    assert len(recorder.bodies) == 1
+
+
+def test_an_extra_input_outside_a_tool_is_not_retried_unless_dropping_params_was_asked_for():
+    recorder = _RecordedAzureAI([_rejection(UNRELATED_REJECTION)])
+
+    with pytest.raises(litellm.BadRequestError):
+        _call_azure_ai(recorder)
+
+    assert len(recorder.bodies) == 1
+
+
+def test_an_extra_input_outside_a_tool_is_retried_when_dropping_params_was_asked_for():
+    recorder = _RecordedAzureAI(
+        [_rejection(UNRELATED_REJECTION), httpx.Response(200, json=A_COMPLETION)]
+    )
+
+    response = _call_azure_ai(recorder, drop_params=True)
+
+    assert len(recorder.bodies) == 2
+    assert response.choices[0].message.content == "sent"
+
+
+@pytest.mark.asyncio
+async def test_a_tool_field_the_provider_rejects_is_dropped_and_retried_on_the_async_path(
+    httpx_transport,
+):
+    import respx
+
+    recorder = _RecordedAzureAI(
+        [_rejection(TOOL_LEVEL_REJECTION), httpx.Response(200, json=A_COMPLETION)]
+    )
+
+    with respx.mock:
+        respx.route(host=AZURE_AI_HOST).mock(side_effect=recorder)
+        response = await litellm.acompletion(
+            model="azure_ai/grok-3",
+            messages=[{"role": "user", "content": "hi"}],
+            tools=[TOOL_WITH_AN_UNSUPPORTED_FIELD],
+            api_base=AZURE_AI_BASE,
+            api_key="fake-key",
+        )
+
+    assert len(recorder.bodies) == 2
+    assert recorder.bodies[0]["tools"][0]["strict"] is True
+    assert "strict" not in recorder.bodies[1]["tools"][0]
+    assert response.choices[0].message.content == "sent"
+
+
+@pytest.mark.asyncio
+async def test_a_provider_that_keeps_rejecting_is_not_retried_forever_on_the_async_path(
+    httpx_transport,
+):
+    import respx
+
+    recorder = _RecordedAzureAI([_rejection(TOOL_LEVEL_REJECTION)])
+
+    with respx.mock:
+        respx.route(host=AZURE_AI_HOST).mock(side_effect=recorder)
+        with pytest.raises(litellm.BadRequestError):
+            await litellm.acompletion(
+                model="azure_ai/grok-3",
+                messages=[{"role": "user", "content": "hi"}],
+                tools=[TOOL_WITH_AN_UNSUPPORTED_FIELD],
+                api_base=AZURE_AI_BASE,
+                api_key="fake-key",
+            )
+
+    assert len(recorder.bodies) == 2