diff --git a/litellm/proxy/guardrails/guardrail_hooks/generic_guardrail_api/generic_guardrail_api.py b/litellm/proxy/guardrails/guardrail_hooks/generic_guardrail_api/generic_guardrail_api.py
index 6b1c9a8b2b3..2186edb1b8d 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/generic_guardrail_api/generic_guardrail_api.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/generic_guardrail_api/generic_guardrail_api.py
@@ -334,6 +334,8 @@ class GenericGuardrailAPI(CustomGuardrail):
             return_inputs["tools"] = guardrail_response.tools
         elif tools:
             return_inputs["tools"] = tools
+        if guardrail_response.structured_messages is not None:
+            return_inputs["structured_messages"] = guardrail_response.structured_messages
         if guardrail_response.stream_holdback_chars is not None:
             return_inputs["stream_holdback_chars"] = guardrail_response.stream_holdback_chars
         return return_inputs
diff --git a/litellm/types/proxy/guardrails/guardrail_hooks/generic_guardrail_api.py b/litellm/types/proxy/guardrails/guardrail_hooks/generic_guardrail_api.py
index 9e198e13902..f98f26a9548 100644
--- a/litellm/types/proxy/guardrails/guardrail_hooks/generic_guardrail_api.py
+++ b/litellm/types/proxy/guardrails/guardrail_hooks/generic_guardrail_api.py
@@ -164,6 +164,7 @@ class GenericGuardrailAPIResponse:
     texts: Optional[List[str]]
     images: Optional[List[str]]
     tools: Optional[List[GuardrailToolParam]]
+    structured_messages: Optional[List[AllMessageValues]]
     action: str
     blocked_reason: Optional[str]
     stream_holdback_chars: Optional[List[int]]
@@ -175,6 +176,7 @@ class GenericGuardrailAPIResponse:
         blocked_reason: Optional[str] = None,
         images: Optional[List[str]] = None,
         tools: Optional[List[GuardrailToolParam]] = None,
+        structured_messages: Optional[List[AllMessageValues]] = None,
         stream_holdback_chars: Optional[List[int]] = None,
     ):
         self.action = action
@@ -182,6 +184,7 @@ class GenericGuardrailAPIResponse:
         self.texts = texts
         self.images = images
         self.tools = tools
+        self.structured_messages = structured_messages
         # Number of trailing chars, indexed the same as ``texts``, that the
         # framework must withhold from streaming emission until the next
         # processing round (word-boundary safety for text transformations).
@@ -199,5 +202,6 @@ class GenericGuardrailAPIResponse:
             texts=data.get("texts"),
             images=data.get("images"),
             tools=data.get("tools"),
+            structured_messages=data.get("structured_messages"),
             stream_holdback_chars=stream_holdback_chars,
         )
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_generic_guardrail_api.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_generic_guardrail_api.py
index 5be0d43c250..e7517be9013 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_generic_guardrail_api.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_generic_guardrail_api.py
@@ -1402,6 +1402,93 @@ class TestGenericGuardrailAPIResponseParsing:
         assert result["texts"] == ["Alice went to Berlin"]
         assert result["stream_holdback_chars"] == [5]
 
+    def test_from_dict_parses_structured_messages(self):
+        from litellm.types.proxy.guardrails.guardrail_hooks.generic_guardrail_api import (
+            GenericGuardrailAPIResponse,
+        )
+
+        compressed = [{"role": "user", "content": "compressed"}]
+        response = GenericGuardrailAPIResponse.from_dict(
+            {"action": "GUARDRAIL_INTERVENED", "structured_messages": compressed}
+        )
+
+        assert response.structured_messages == compressed
+
+    def test_from_dict_structured_messages_absent_is_none(self):
+        from litellm.types.proxy.guardrails.guardrail_hooks.generic_guardrail_api import (
+            GenericGuardrailAPIResponse,
+        )
+
+        response = GenericGuardrailAPIResponse.from_dict({"action": "NONE", "texts": ["hi"]})
+
+        assert response.structured_messages is None
+
+    @pytest.mark.asyncio
+    async def test_apply_guardrail_flows_structured_messages_back_to_inputs(self, generic_guardrail):
+        """A guardrail that rewrites the whole conversation (e.g. prompt compression)
+        returns new structured_messages; they must be surfaced on the returned inputs
+        so the framework can send the compressed conversation to the LLM instead of the
+        original. Regression: previously the response's structured_messages were dropped."""
+        original = [
+            {"role": "user", "content": "a very long log " * 500},
+            {"role": "user", "content": "summarize"},
+        ]
+        compressed = [
+            {"role": "user", "content": "a very long log [compressed]"},
+            {"role": "user", "content": "summarize"},
+        ]
+        mock_response = MagicMock()
+        mock_response.json.return_value = {
+            "action": "GUARDRAIL_INTERVENED",
+            "structured_messages": compressed,
+        }
+        mock_response.raise_for_status = MagicMock()
+
+        with patch.object(generic_guardrail.async_handler, "post", return_value=mock_response):
+            result = await generic_guardrail.apply_guardrail(
+                inputs={"texts": [m["content"] for m in original], "structured_messages": original},
+                request_data={},
+                input_type="request",
+            )
+
+        assert result["structured_messages"] == compressed
+
+    @pytest.mark.asyncio
+    async def test_compressed_structured_messages_are_written_back_to_request(self, generic_guardrail):
+        """End-to-end pre-call write-back: when the guardrail returns compressed
+        structured_messages, the chat-completions handler must replace data["messages"]
+        with them so the compressed conversation is what reaches the LLM."""
+        from litellm.llms.openai.chat.guardrail_translation.handler import (
+            OpenAIChatCompletionsHandler,
+        )
+
+        compressed = [
+            {"role": "user", "content": "log summary [400 matches compressed to 5]"},
+            {"role": "user", "content": "summarize"},
+        ]
+        mock_response = MagicMock()
+        mock_response.json.return_value = {
+            "action": "GUARDRAIL_INTERVENED",
+            "structured_messages": compressed,
+        }
+        mock_response.raise_for_status = MagicMock()
+
+        data = {
+            "model": "gpt-4",
+            "messages": [
+                {"role": "user", "content": "a very long log " * 500},
+                {"role": "user", "content": "summarize"},
+            ],
+        }
+
+        with patch.object(generic_guardrail.async_handler, "post", return_value=mock_response):
+            result = await OpenAIChatCompletionsHandler().process_input_messages(
+                data=data,
+                guardrail_to_apply=generic_guardrail,
+            )
+
+        assert result["messages"] == compressed
+
 
 class TestGenericGuardrailAPIStreamingViaUnified:
     """Streaming output checks routed through UnifiedLLMGuardrails."""