diff --git a/litellm/proxy/guardrails/guardrail_hooks/grayswan/grayswan.py b/litellm/proxy/guardrails/guardrail_hooks/grayswan/grayswan.py
index b14b3f1a0af..f32228a6204 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/grayswan/grayswan.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/grayswan/grayswan.py
@@ -277,7 +277,7 @@ class GraySwanGuardrail(CustomGuardrail):
         role: Final = "assistant" if input_type == "response" else "user"
         merged_tail: Final = (
             _MonitorMessage(role="assistant", content=texts[-1], tool_calls=response_tool_calls)
-            if texts and response_tool_calls
+            if len(texts) == 1 and response_tool_calls
             else None
         )
         messages: Final = (
@@ -286,7 +286,7 @@ class GraySwanGuardrail(CustomGuardrail):
             *((merged_tail,) if merged_tail else ()),
             *(
                 (_MonitorMessage(role="assistant", tool_calls=response_tool_calls),)
-                if response_tool_calls and not texts
+                if response_tool_calls and not merged_tail
                 else ()
             ),
         )
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_grayswan.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_grayswan.py
index a3d7f9e73ef..4c32c0bbd55 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_grayswan.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_grayswan.py
@@ -772,6 +772,33 @@ async def test_post_call_merges_response_text_and_tool_calls_into_one_message()
     ]
 
 
+@pytest.mark.asyncio
+async def test_post_call_multi_choice_texts_and_tool_calls_stay_split() -> None:
+    guardrail = _post_call_guardrail()
+    client = _CapturingClient()
+    guardrail.async_handler = client
+
+    tool_call = {
+        "id": "call_send",
+        "type": "function",
+        "function": {"name": "send_email", "arguments": '{"to": "cfo@example.com"}'},
+    }
+    await guardrail.apply_guardrail(
+        inputs={"texts": ["first answer", "second answer"], "tool_calls": [tool_call]},
+        request_data={**_REQUEST_DATA, "litellm_logging_obj": _LoggingObj("acompletion")},
+        input_type="response",
+        logging_obj=_LoggingObj("acompletion"),
+    )
+
+    messages = list(client.calls[0]["json"]["messages"])
+    assert messages == [
+        *_REQUEST_DATA["messages"],
+        {"role": "assistant", "content": "first answer"},
+        {"role": "assistant", "content": "second answer"},
+        {"role": "assistant", "tool_calls": (tool_call,)},
+    ]
+
+
 @pytest.mark.asyncio
 async def test_post_call_prefers_request_route_over_logging_call_type() -> None:
     guardrail = _post_call_guardrail()