diff --git a/litellm/litellm_core_utils/streaming_handler.py b/litellm/litellm_core_utils/streaming_handler.py
index f3274151e5a..486c95e227e 100644
--- a/litellm/litellm_core_utils/streaming_handler.py
+++ b/litellm/litellm_core_utils/streaming_handler.py
@@ -2318,8 +2318,15 @@ class CustomStreamWrapper:
 
         429 (rate-limit) is explicitly exempted from the 4xx filter because
         it is transient and the Router should switch to another model group.
+        Context-window and content-policy errors are also exempted because
+        the Router has dedicated fallback configs for them
+        (context_window_fallbacks / content_policy_fallbacks).
         """
-        from litellm.exceptions import MidStreamFallbackError
+        from litellm.exceptions import (
+            ContentPolicyViolationError,
+            ContextWindowExceededError,
+            MidStreamFallbackError,
+        )
 
         # Map to OpenAI exception format
         if isinstance(e, OpenAIError):
@@ -2358,19 +2365,27 @@ class CustomStreamWrapper:
         mapped_status_code = _normalize_status_code(mapped_exception)
         original_status_code = _normalize_status_code(e)
 
+        has_dedicated_fallback_config = isinstance(
+            mapped_exception,
+            (ContentPolicyViolationError, ContextWindowExceededError),
+        )
+
         # Raise non-retriable client errors directly (skip fallback).
         # Exception: 429 (rate-limit) IS retriable/transient — allow it
         # through so the Router can switch to a different model group.
+        # Same for errors with dedicated fallback configs.
         if (
             mapped_status_code is not None
             and 400 <= mapped_status_code < 500
             and mapped_status_code != 429
+            and not has_dedicated_fallback_config
         ):
             raise mapped_exception
         if (
             original_status_code is not None
             and 400 <= original_status_code < 500
             and original_status_code != 429
+            and not has_dedicated_fallback_config
         ):
             raise mapped_exception
 
diff --git a/litellm/router.py b/litellm/router.py
index d0f4e5ff44d..dec88c0238b 100644
--- a/litellm/router.py
+++ b/litellm/router.py
@@ -2196,9 +2196,21 @@ class Router:
                     self._update_kwargs_before_fallbacks(
                         model=model_group, kwargs=initial_kwargs
                     )
+                    # Unwrap errors with dedicated fallback configs so the
+                    # isinstance checks in the common utils can route them to
+                    # context_window_fallbacks / content_policy_fallbacks.
+                    fallback_trigger_exception: Exception = e
+                    if isinstance(
+                        e.original_exception,
+                        (
+                            litellm.ContextWindowExceededError,
+                            litellm.ContentPolicyViolationError,
+                        ),
+                    ):
+                        fallback_trigger_exception = e.original_exception
                     fallback_response = (
                         await self.async_function_with_fallbacks_common_utils(
-                            e=e,
+                            e=fallback_trigger_exception,
                             disable_fallbacks=False,
                             fallbacks=fallbacks,
                             context_window_fallbacks=context_window_fallbacks,
diff --git a/tests/test_litellm/litellm_core_utils/test_streaming_handler.py b/tests/test_litellm/litellm_core_utils/test_streaming_handler.py
index b2002f9a0f9..692c207003b 100644
--- a/tests/test_litellm/litellm_core_utils/test_streaming_handler.py
+++ b/tests/test_litellm/litellm_core_utils/test_streaming_handler.py
@@ -876,6 +876,41 @@ def test_sync_streaming_bad_request_not_midstream(logging_obj: Logging):
     assert "invalid maxOutputTokens" in str(excinfo.value)
 
 
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "exception_class",
+    [litellm.ContentPolicyViolationError, litellm.ContextWindowExceededError],
+)
+async def test_streaming_dedicated_fallback_error_triggers_midstream_fallback(
+    logging_obj: Logging, exception_class
+):
+    """400s with dedicated fallback configs (content_policy_fallbacks /
+    context_window_fallbacks) must wrap into MidStreamFallbackError instead
+    of raising directly, so the Router's fallback chain can engage.
+    Regression test for https://github.com/BerriAI/litellm/issues/28599
+    """
+    from litellm.exceptions import MidStreamFallbackError
+
+    async def _raise_dedicated_fallback_error(**kwargs):
+        raise exception_class(
+            message="content blocked", model="gpt-4", llm_provider="openai"
+        )
+
+    response = CustomStreamWrapper(
+        completion_stream=None,
+        model="gpt-4",
+        logging_obj=logging_obj,
+        custom_llm_provider="openai",
+        make_call=_raise_dedicated_fallback_error,
+    )
+
+    with pytest.raises(MidStreamFallbackError) as excinfo:
+        await response.__anext__()
+
+    assert isinstance(excinfo.value.original_exception, exception_class)
+    assert excinfo.value.status_code == 400
+
+
 @pytest.mark.asyncio
 async def test_async_streaming_read_timeout_triggers_midstream_fallback(
     logging_obj: Logging,
diff --git a/tests/test_litellm/test_router.py b/tests/test_litellm/test_router.py
index cd235d8de67..223206ab5b3 100644
--- a/tests/test_litellm/test_router.py
+++ b/tests/test_litellm/test_router.py
@@ -1623,6 +1623,62 @@ async def test_acompletion_streaming_iterator_preserves_hidden_params():
     assert result._hidden_params.get("_response_ms") == 500.0
 
 
+@pytest.mark.asyncio
+async def test_acompletion_streaming_iterator_unwraps_content_policy_violation():
+    """A MidStreamFallbackError wrapping a ContentPolicyViolationError must
+    pass the original exception to the fallback utils, so the dedicated
+    content_policy_fallbacks branch matches on its isinstance check.
+    Regression test for https://github.com/BerriAI/litellm/issues/28599
+    """
+    from litellm.exceptions import ContentPolicyViolationError, MidStreamFallbackError
+
+    cpv_error = ContentPolicyViolationError(
+        message="content blocked", model="gpt-4", llm_provider="openai"
+    )
+    mid_stream_error = MidStreamFallbackError(
+        message=str(cpv_error),
+        model="gpt-4",
+        llm_provider="openai",
+        original_exception=cpv_error,
+        is_pre_first_chunk=True,
+    )
+
+    class FailingStream:
+        model = "gpt-4"
+        custom_llm_provider = "openai"
+        logging_obj = MagicMock()
+        chunks = []
+
+        def __aiter__(self):
+            return self
+
+        async def __anext__(self):
+            raise mid_stream_error
+
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "gpt-4",
+                "litellm_params": {"model": "gpt-4", "api_key": "fake-key"},
+            }
+        ],
+        content_policy_fallbacks=[{"gpt-4": ["gpt-3.5-turbo"]}],
+    )
+
+    with patch.object(
+        router, "async_function_with_fallbacks_common_utils", return_value=object()
+    ) as mock_fallback_utils:
+        result = await router._acompletion_streaming_iterator(
+            model_response=FailingStream(),
+            messages=[{"role": "user", "content": "Hello"}],
+            initial_kwargs={"model": "gpt-4", "stream": True},
+        )
+        async for _ in result:
+            pass
+
+    assert mock_fallback_utils.call_args.kwargs["e"] is cpv_error
+
+
 def test_completion_streaming_iterator_fallback_on_429():
     """Sync streaming: MidStreamFallbackError (429 pre-first-chunk) triggers fallback.