diff --git a/litellm/proxy/guardrails/guardrail_hooks/litellm_content_filter/content_filter.py b/litellm/proxy/guardrails/guardrail_hooks/litellm_content_filter/content_filter.py
index 1ffe200169a..a210762d1df 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/litellm_content_filter/content_filter.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/litellm_content_filter/content_filter.py
@@ -1963,7 +1963,17 @@ class ContentFilterGuardrail(CustomGuardrail):
                 exception_str=exception_str,
             )
 
-    def _trim_streamed_choice_buffer(self, state: _StreamedChoiceState, masked_text: str) -> _StreamedChoiceState:
+    def _streamed_scan_context_chars(self) -> int:
+        """Retained tail length: the default context, widened to the longest configured keyword."""
+        longest_keyword: Final = max(
+            map(len, (*self.blocked_words, *self.category_keywords, *self.always_block_category_keywords)),
+            default=0,
+        )
+        return max(CONTENT_FILTER_STREAMING_SCAN_CONTEXT_CHARS, longest_keyword)
+
+    def _trim_streamed_choice_buffer(
+        self, state: _StreamedChoiceState, masked_text: str, scan_context_chars: int
+    ) -> _StreamedChoiceState:
         """
         Bound the per-choice buffer rescanned on every streamed chunk.
 
@@ -1974,10 +1984,10 @@ class ContentFilterGuardrail(CustomGuardrail):
 
         Detections found in the dropped prefix move to the state's committed detections.
         """
-        if len(state.buffered_text) <= 2 * CONTENT_FILTER_STREAMING_SCAN_CONTEXT_CHARS:
+        if len(state.buffered_text) <= 2 * scan_context_chars:
             return state
-        head: Final = state.buffered_text[:-CONTENT_FILTER_STREAMING_SCAN_CONTEXT_CHARS]
-        tail: Final = state.buffered_text[-CONTENT_FILTER_STREAMING_SCAN_CONTEXT_CHARS:]
+        head: Final = state.buffered_text[:-scan_context_chars]
+        tail: Final = state.buffered_text[-scan_context_chars:]
         head_detections: Final[list[ContentFilterDetection]] = []  # mutable-ok: filled by _filter_single_text
         try:
             masked_head: Final = self._filter_single_text(head, detections=head_detections)
@@ -2016,6 +2026,7 @@ class ContentFilterGuardrail(CustomGuardrail):
         contract.
         """
         state_by_choice: Final[dict[int, _StreamedChoiceState]] = {}
+        scan_context_chars: Final = self._streamed_scan_context_chars()
 
         start_time: Final = datetime.now()
         scan_seconds: float = 0.0  # rebind-ok: accumulates per-chunk scan time across the stream
@@ -2085,7 +2096,9 @@ class ContentFilterGuardrail(CustomGuardrail):
                             continue
 
                         trim_started = time.perf_counter()
-                        state_by_choice[choice_index] = self._trim_streamed_choice_buffer(next_state, masked_text)
+                        state_by_choice[choice_index] = self._trim_streamed_choice_buffer(
+                            next_state, masked_text, scan_context_chars
+                        )
                         scan_seconds += time.perf_counter() - trim_started
 
                     yield item
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/content_filter/test_content_filter.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/content_filter/test_content_filter.py
index 71f46ca3047..b91abb98dbf 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/content_filter/test_content_filter.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/content_filter/test_content_filter.py
@@ -1009,6 +1009,33 @@ class TestContentFilterGuardrail:
         assert entry["guardrail_status"] == "guardrail_intervened"
         assert [d["keyword"] for d in entry["guardrail_response"]] == [phrase]
 
+    @pytest.mark.asyncio
+    async def test_streaming_hook_blocks_keyword_longer_than_scan_context(self):
+        """
+        A blocked keyword longer than the default retained context arrives after
+        enough text that the buffer has already been trimmed at least once. The
+        retained tail must be wide enough that the keyword's start is still in the
+        buffer when its end arrives, so the stream is blocked.
+        """
+        phrase = " ".join(f"token{i:03d}" for i in range(80))
+        assert len(phrase) > CONTENT_FILTER_STREAMING_SCAN_CONTEXT_CHARS
+        guardrail = ContentFilterGuardrail(
+            guardrail_name="test-streaming-keyword-wider-than-context",
+            blocked_words=[BlockedWord(keyword=phrase, action=ContentFilterAction.BLOCK)],
+            event_hook=GuardrailEventHooks.post_call,
+        )
+        filler = "plain filler sentence. " * (3 * CONTENT_FILTER_STREAMING_SCAN_CONTEXT_CHARS // 23)
+        text = filler + phrase + " and that is all."
+        chunks = [text[i : i + 16] for i in range(0, len(text), 16)]
+        request_data = {"messages": [], "model": "gpt-4o", "metadata": {}}
+
+        with pytest.raises(HTTPException) as exc_info:
+            await self._collect_streamed_text(guardrail, chunks, request_data)
+
+        assert exc_info.value.detail["keyword"] == phrase
+        entry = request_data["metadata"]["standard_logging_guardrail_information"][0]
+        assert entry["guardrail_status"] == "guardrail_intervened"
+
     @pytest.mark.asyncio
     async def test_streaming_hook_masks_every_email_in_long_stream_and_logs_once(
         self,