diff --git a/litellm/llms/anthropic/experimental_pass_through/messages/handler.py b/litellm/llms/anthropic/experimental_pass_through/messages/handler.py
index 9d1e921cce4..9050a9405c8 100644
--- a/litellm/llms/anthropic/experimental_pass_through/messages/handler.py
+++ b/litellm/llms/anthropic/experimental_pass_through/messages/handler.py
@@ -68,10 +68,23 @@ def _responses_mode_is_lost_by_prefix_strip(
     )
 
 
+def _points_at_openai_backend(api_base: str | None) -> bool:
+    """Whether api_base is unset or targets api.openai.com rather than a self-hosted backend.
+
+    The ``openai/`` prefix is also how OpenAI-compatible servers (vLLM, llama.cpp, SGLang, ...)
+    are declared. Those set a custom api_base and do not implement the Responses API, so bridging
+    /v1/messages to it there breaks multimodal requests.
+    """
+    if not api_base:
+        return True
+    return "api.openai.com" in api_base
+
+
 def _should_route_to_responses_api(
     custom_llm_provider: str | None,
     requested_model: str | None = None,
     resolved_model: str | None = None,
+    api_base: str | None = None,
 ) -> bool:
     """Return True when the request should use the Responses API path.
 
@@ -81,7 +94,7 @@ def _should_route_to_responses_api(
     if litellm.use_chat_completions_url_for_anthropic_messages:
         return False
     if custom_llm_provider in _RESPONSES_API_PROVIDERS:
-        return True
+        return _points_at_openai_backend(api_base)
     if custom_llm_provider is None or requested_model is None or resolved_model is None:
         return False
     return _responses_mode_is_lost_by_prefix_strip(requested_model, resolved_model, custom_llm_provider)
@@ -578,7 +591,7 @@ def anthropic_messages_handler(
         )
     if anthropic_messages_provider_config is None:
         # Route to Responses API for OpenAI / Azure, chat/completions for everything else.
-        if _should_route_to_responses_api(custom_llm_provider, original_model, model):
+        if _should_route_to_responses_api(custom_llm_provider, original_model, model, dynamic_api_base or api_base):
             return LiteLLMMessagesToResponsesAPIHandler.anthropic_messages_handler(
                 max_tokens=max_tokens,
                 messages=messages,
diff --git a/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_anthropic_experimental_pass_through_messages_handler.py b/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_anthropic_experimental_pass_through_messages_handler.py
index 01f7a2fb7ab..9f73fdfed15 100644
--- a/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_anthropic_experimental_pass_through_messages_handler.py
+++ b/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_anthropic_experimental_pass_through_messages_handler.py
@@ -137,6 +137,27 @@ def test_anthropic_experimental_pass_through_messages_handler_dynamic_api_key_an
         assert mock_completion.call_args.kwargs["custom_key"] == "custom_value"
 
 
+@pytest.mark.parametrize(
+    "api_base, expected",
+    [
+        (None, True),
+        ("https://api.openai.com/v1", True),
+        ("http://localhost:8000/v1", False),
+        ("http://vllm-host:8000/v1", False),
+    ],
+)
+def test_should_route_to_responses_api_considers_api_base_for_openai(api_base, expected):
+    """Regression test for #40780. A self-hosted OpenAI-compatible backend declared as
+    ``openai/<model>`` with a custom api_base must not be routed to the OpenAI Responses API
+    (which reshapes images into ``input_image`` items the backend rejects); only real OpenAI
+    (api_base unset or api.openai.com) keeps the Responses API path."""
+    from litellm.llms.anthropic.experimental_pass_through.messages.handler import (
+        _should_route_to_responses_api,
+    )
+
+    assert _should_route_to_responses_api("openai", "openai/model", "model", api_base) is expected
+
+
 @pytest.mark.asyncio
 async def test_anthropic_messages_sanitizes_empty_text_blocks_before_dispatch():
     """Regression test for #22930.  The unified /v1/messages path must