diff --git a/src/strands/models/litellm.py b/src/strands/models/litellm.py
index 005eed3df..1763f5dec 100644
--- a/src/strands/models/litellm.py
+++ b/src/strands/models/litellm.py
@@ -8,11 +8,13 @@
 from typing import Any, AsyncGenerator, Optional, Type, TypedDict, TypeVar, Union, cast
 
 import litellm
+from litellm.exceptions import ContextWindowExceededError
 from litellm.utils import supports_response_schema
 from pydantic import BaseModel
 from typing_extensions import Unpack, override
 
 from ..types.content import ContentBlock, Messages
+from ..types.exceptions import ContextWindowOverflowException
 from ..types.streaming import StreamEvent
 from ..types.tools import ToolChoice, ToolSpec
 from ._validation import validate_config_keys
@@ -135,7 +137,11 @@ async def stream(
         logger.debug("request=<%s>", request)
 
         logger.debug("invoking model")
-        response = await litellm.acompletion(**self.client_args, **request)
+        try:
+            response = await litellm.acompletion(**self.client_args, **request)
+        except ContextWindowExceededError as e:
+            logger.warning("litellm client raised context window overflow")
+            raise ContextWindowOverflowException(e) from e
 
         logger.debug("got response from model")
         yield self.format_chunk({"chunk_type": "message_start"})
@@ -205,15 +211,24 @@ async def structured_output(
         Yields:
             Model events with the last being the structured output.
         """
-        if not supports_response_schema(self.get_config()["model_id"]):
+        supports_schema = supports_response_schema(self.get_config()["model_id"])
+
+        # If the provider does not support response schemas, we cannot reliably parse structured output.
+        # In that case we must not call the provider and must raise the documented ValueError.
+        if not supports_schema:
             raise ValueError("Model does not support response_format")
 
-        response = await litellm.acompletion(
-            **self.client_args,
-            model=self.get_config()["model_id"],
-            messages=self.format_request(prompt, system_prompt=system_prompt)["messages"],
-            response_format=output_model,
-        )
+        # For providers that DO support response schemas, call litellm and map context-window errors.
+        try:
+            response = await litellm.acompletion(
+                **self.client_args,
+                model=self.get_config()["model_id"],
+                messages=self.format_request(prompt, system_prompt=system_prompt)["messages"],
+                response_format=output_model,
+            )
+        except ContextWindowExceededError as e:
+            logger.warning("litellm client raised context window overflow in structured_output")
+            raise ContextWindowOverflowException(e) from e
 
         if len(response.choices) > 1:
             raise ValueError("Multiple choices found in the response.")
diff --git a/tests/strands/models/test_litellm.py b/tests/strands/models/test_litellm.py
index bc81fc819..776ae7bae 100644
--- a/tests/strands/models/test_litellm.py
+++ b/tests/strands/models/test_litellm.py
@@ -3,9 +3,11 @@
 
 import pydantic
 import pytest
+from litellm.exceptions import ContextWindowExceededError
 
 import strands
 from strands.models.litellm import LiteLLMModel
+from strands.types.exceptions import ContextWindowOverflowException
 
 
 @pytest.fixture
@@ -332,3 +334,13 @@ def test_tool_choice_none_no_warning(model, messages, captured_warnings):
     model.format_request(messages, tool_choice=None)
 
     assert len(captured_warnings) == 0
+
+
+@pytest.mark.asyncio
+async def test_context_window_maps_to_typed_exception(litellm_acompletion, model):
+    """Test that a typed ContextWindowExceededError is mapped correctly."""
+    litellm_acompletion.side_effect = ContextWindowExceededError(message="test error", model="x", llm_provider="y")
+
+    with pytest.raises(ContextWindowOverflowException):
+        async for _ in model.stream([{"role": "user", "content": [{"text": "x"}]}]):
+            pass