diff --git a/autogen/agentchat/conversable_agent.py b/autogen/agentchat/conversable_agent.py
index 20398965c..2ca06e2fe 100644
--- a/autogen/agentchat/conversable_agent.py
+++ b/autogen/agentchat/conversable_agent.py
@@ -2259,30 +2259,54 @@ class ConversableAgent(LLMAgent):
         """
         if message is None:
             message = self.get_human_input(">")
-        if isinstance(message, str):
-            return self._process_carryover(message, kwargs)
-        elif isinstance(message, dict):
-            message = message.copy()
-            # TODO: Do we need to do the following?
-            # if message.get("content") is None:
-            #     message["content"] = self.get_human_input(">")
-            message["content"] = self._process_carryover(message.get("content", ""), kwargs)
+
+        return self._handle_carryover(message, kwargs)
+
+    def _handle_carryover(self, message: Union[str, Dict], kwargs: dict) -> Union[str, Dict]:
+        if not kwargs.get("carryover"):
             return message
 
-    def _process_carryover(self, message: str, kwargs: dict) -> str:
-        carryover = kwargs.get("carryover")
-        if carryover:
-            # if carryover is string
-            if isinstance(carryover, str):
-                message += "\nContext: \n" + carryover
-            elif isinstance(carryover, list):
-                message += "\nContext: \n" + ("\n").join([t for t in carryover])
-            else:
-                raise InvalidCarryOverType(
-                    "Carryover should be a string or a list of strings. Not adding carryover to the message."
-                )
+        if isinstance(message, str):
+            return self._process_carryover(message, kwargs)
+
+        elif isinstance(message, dict):
+            if isinstance(message.get("content"), str):
+                # Makes sure the original message is not mutated
+                message = message.copy()
+                message["content"] = self._process_carryover(message["content"], kwargs)
+            elif isinstance(message.get("content"), list):
+                # Makes sure the original message is not mutated
+                message = message.copy()
+                message["content"] = self._process_multimodal_carryover(message["content"], kwargs)
+        else:
+            raise InvalidCarryOverType("Carryover should be a string or a list of strings.")
+
         return message
 
+    def _process_carryover(self, content: str, kwargs: dict) -> str:
+        # Makes sure there's a carryover
+        if not kwargs.get("carryover"):
+            return content
+
+        # if carryover is string
+        if isinstance(kwargs["carryover"], str):
+            content += "\nContext: \n" + kwargs["carryover"]
+        elif isinstance(kwargs["carryover"], list):
+            content += "\nContext: \n" + ("\n").join([t for t in kwargs["carryover"]])
+        else:
+            raise InvalidCarryOverType(
+                "Carryover should be a string or a list of strings. Not adding carryover to the message."
+            )
+        return content
+
+    def _process_multimodal_carryover(self, content: List[Dict], kwargs: dict) -> List[Dict]:
+        """Prepends the context to a multimodal message."""
+        # Makes sure there's a carryover
+        if not kwargs.get("carryover"):
+            return content
+
+        return [{"type": "text", "text": self._process_carryover("", kwargs)}] + content
+
     async def a_generate_init_message(self, message: Union[Dict, str, None], **kwargs) -> Union[str, Dict]:
         """Generate the initial message for the agent.
         If message is None, input() will be called to get the initial message.
@@ -2295,12 +2319,8 @@ class ConversableAgent(LLMAgent):
         """
         if message is None:
             message = await self.a_get_human_input(">")
-        if isinstance(message, str):
-            return self._process_carryover(message, kwargs)
-        elif isinstance(message, dict):
-            message = message.copy()
-            message["content"] = self._process_carryover(message["content"], kwargs)
-            return message
+
+        return self._handle_carryover(message, kwargs)
 
     def register_function(self, function_map: Dict[str, Union[Callable, None]]):
         """Register functions to the agent.
diff --git a/test/agentchat/test_conversable_agent.py b/test/agentchat/test_conversable_agent.py
index 6d9c1ac32..5ff2c0c10 100755
--- a/test/agentchat/test_conversable_agent.py
+++ b/test/agentchat/test_conversable_agent.py
@@ -1263,6 +1263,54 @@ def test_messages_with_carryover():
     with pytest.raises(InvalidCarryOverType):
         agent1.generate_init_message(**context)
 
+    # Test multimodal messages
+    mm_content = [
+        {"type": "text", "text": "hello"},
+        {"type": "text", "text": "goodbye"},
+        {
+            "type": "image_url",
+            "image_url": {"url": "https://example.com/image.png"},
+        },
+    ]
+    mm_message = {"content": mm_content}
+    context = dict(
+        message=mm_message,
+        carryover="Testing carryover.",
+    )
+    generated_message = agent1.generate_init_message(**context)
+    assert isinstance(generated_message, dict)
+    assert len(generated_message["content"]) == 4
+
+    context = dict(message=mm_message, carryover=["Testing carryover.", "This should pass"])
+    generated_message = agent1.generate_init_message(**context)
+    assert isinstance(generated_message, dict)
+    assert len(generated_message["content"]) == 4
+
+    context = dict(message=mm_message, carryover=3)
+    with pytest.raises(InvalidCarryOverType):
+        agent1.generate_init_message(**context)
+
+    # Test without carryover
+    print(mm_message)
+    context = dict(message=mm_message)
+    generated_message = agent1.generate_init_message(**context)
+    assert isinstance(generated_message, dict)
+    assert len(generated_message["content"]) == 3
+
+    # Test without text in multimodal message
+    mm_content = [
+        {"type": "image_url", "image_url": {"url": "https://example.com/image.png"}},
+    ]
+    mm_message = {"content": mm_content}
+    context = dict(message=mm_message)
+    generated_message = agent1.generate_init_message(**context)
+    assert isinstance(generated_message, dict)
+    assert len(generated_message["content"]) == 1
+
+    generated_message = agent1.generate_init_message(**context, carryover="Testing carryover.")
+    assert isinstance(generated_message, dict)
+    assert len(generated_message["content"]) == 2
+
 
 if __name__ == "__main__":
     # test_trigger()