diff --git a/libs/partners/openai/langchain_openai/chat_models/base.py b/libs/partners/openai/langchain_openai/chat_models/base.py
index ea4df08969..50308b6327 100644
--- a/libs/partners/openai/langchain_openai/chat_models/base.py
+++ b/libs/partners/openai/langchain_openai/chat_models/base.py
@@ -2,6 +2,7 @@
 
 from __future__ import annotations
 
+import json
 import logging
 import os
 import sys
@@ -50,8 +51,10 @@ from langchain_core.messages import (
     FunctionMessageChunk,
     HumanMessage,
     HumanMessageChunk,
+    InvalidToolCall,
     SystemMessage,
     SystemMessageChunk,
+    ToolCall,
     ToolMessage,
     ToolMessageChunk,
 )
@@ -169,20 +172,25 @@ def _convert_message_to_dict(message: BaseMessage) -> dict:
         message_dict["role"] = "assistant"
         if "function_call" in message.additional_kwargs:
             message_dict["function_call"] = message.additional_kwargs["function_call"]
-            # If function call only, content is None not empty string
-            if message_dict["content"] == "":
-                message_dict["content"] = None
-        if "tool_calls" in message.additional_kwargs:
+        if message.tool_calls or message.invalid_tool_calls:
+            message_dict["tool_calls"] = [
+                _lc_tool_call_to_openai_tool_call(tc) for tc in message.tool_calls
+            ] + [
+                _lc_invalid_tool_call_to_openai_tool_call(tc)
+                for tc in message.invalid_tool_calls
+            ]
+        elif "tool_calls" in message.additional_kwargs:
             message_dict["tool_calls"] = message.additional_kwargs["tool_calls"]
-            # If tool calls only, content is None not empty string
-            if message_dict["content"] == "":
-                message_dict["content"] = None
-
             tool_call_supported_props = {"id", "type", "function"}
             message_dict["tool_calls"] = [
                 {k: v for k, v in tool_call.items() if k in tool_call_supported_props}
                 for tool_call in message_dict["tool_calls"]
             ]
+        else:
+            pass
+        # If tool calls present, content null value should be None not empty string.
+        if "function_call" in message_dict or "tool_calls" in message_dict:
+            message_dict["content"] = message_dict["content"] or None
     elif isinstance(message, SystemMessage):
         message_dict["role"] = "system"
     elif isinstance(message, FunctionMessage):
@@ -1067,3 +1075,27 @@ class ChatOpenAI(BaseChatModel):
 
 def _is_pydantic_class(obj: Any) -> bool:
     return isinstance(obj, type) and issubclass(obj, BaseModel)
+
+
+def _lc_tool_call_to_openai_tool_call(tool_call: ToolCall) -> dict:
+    return {
+        "type": "function",
+        "id": tool_call["id"],
+        "function": {
+            "name": tool_call["name"],
+            "arguments": json.dumps(tool_call["args"]),
+        },
+    }
+
+
+def _lc_invalid_tool_call_to_openai_tool_call(
+    invalid_tool_call: InvalidToolCall,
+) -> dict:
+    return {
+        "type": "function",
+        "id": invalid_tool_call["id"],
+        "function": {
+            "name": invalid_tool_call["name"],
+            "arguments": invalid_tool_call["args"],
+        },
+    }
diff --git a/libs/partners/openai/tests/integration_tests/chat_models/test_base.py b/libs/partners/openai/tests/integration_tests/chat_models/test_base.py
index 03cdcbee6c..e1f15ec9c5 100644
--- a/libs/partners/openai/tests/integration_tests/chat_models/test_base.py
+++ b/libs/partners/openai/tests/integration_tests/chat_models/test_base.py
@@ -10,6 +10,7 @@ from langchain_core.messages import (
     BaseMessageChunk,
     HumanMessage,
     SystemMessage,
+    ToolCall,
     ToolMessage,
 )
 from langchain_core.outputs import (
@@ -519,6 +520,49 @@ def test_tool_use() -> None:
     llm_with_tool.invoke(msgs)
 
 
+def test_manual_tool_call_msg() -> None:
+    """Test passing in manually construct tool call message."""
+    llm = ChatOpenAI(model="gpt-3.5-turbo-0125", temperature=0)
+    llm_with_tool = llm.bind_tools(tools=[GenerateUsername])
+    msgs: List = [
+        HumanMessage("Sally has green hair, what would her username be?"),
+        AIMessage(
+            content="",
+            tool_calls=[
+                ToolCall(
+                    name="GenerateUsername",
+                    args={"name": "Sally", "hair_color": "green"},
+                    id="foo",
+                )
+            ],
+        ),
+        ToolMessage("sally_green_hair", tool_call_id="foo"),
+    ]
+    output: AIMessage = cast(AIMessage, llm_with_tool.invoke(msgs))
+    assert output.content
+    # Should not have called the tool again.
+    assert not output.tool_calls and not output.invalid_tool_calls
+
+    # OpenAI should error when tool call id doesn't match across AIMessage and
+    # ToolMessage
+    msgs = [
+        HumanMessage("Sally has green hair, what would her username be?"),
+        AIMessage(
+            content="",
+            tool_calls=[
+                ToolCall(
+                    name="GenerateUsername",
+                    args={"name": "Sally", "hair_color": "green"},
+                    id="bar",
+                )
+            ],
+        ),
+        ToolMessage("sally_green_hair", tool_call_id="foo"),
+    ]
+    with pytest.raises(Exception):
+        llm_with_tool.invoke(msgs)
+
+
 def test_openai_structured_output() -> None:
     class MyModel(BaseModel):
         """A Person"""
diff --git a/libs/partners/openai/tests/unit_tests/chat_models/test_base.py b/libs/partners/openai/tests/unit_tests/chat_models/test_base.py
index 1b8668c955..9665af8f64 100644
--- a/libs/partners/openai/tests/unit_tests/chat_models/test_base.py
+++ b/libs/partners/openai/tests/unit_tests/chat_models/test_base.py
@@ -104,7 +104,7 @@ def test__convert_dict_to_message_tool_call() -> None:
     raw_tool_call = {
         "id": "call_wm0JY6CdwOMZ4eTxHWUThDNz",
         "function": {
-            "arguments": '{"name":"Sally","hair_color":"green"}',
+            "arguments": '{"name": "Sally", "hair_color": "green"}',
             "name": "GenerateUsername",
         },
         "type": "function",
@@ -126,7 +126,7 @@ def test__convert_dict_to_message_tool_call() -> None:
     assert _convert_message_to_dict(expected_output) == message
 
     # Test malformed tool call
-    raw_tool_calls = [
+    raw_tool_calls: list = [
         {
             "id": "call_wm0JY6CdwOMZ4eTxHWUThDNz",
             "function": {
@@ -138,12 +138,13 @@ def test__convert_dict_to_message_tool_call() -> None:
         {
             "id": "call_abc123",
             "function": {
-                "arguments": '{"name":"Sally","hair_color":"green"}',
+                "arguments": '{"name": "Sally", "hair_color": "green"}',
                 "name": "GenerateUsername",
             },
             "type": "function",
         },
     ]
+    raw_tool_calls = list(sorted(raw_tool_calls, key=lambda x: x["id"]))
     message = {"role": "assistant", "content": None, "tool_calls": raw_tool_calls}
     result = _convert_dict_to_message(message)
     expected_output = AIMessage(
@@ -166,7 +167,11 @@ def test__convert_dict_to_message_tool_call() -> None:
         ],
     )
     assert result == expected_output
-    assert _convert_message_to_dict(expected_output) == message
+    reverted_message_dict = _convert_message_to_dict(expected_output)
+    reverted_message_dict["tool_calls"] = list(
+        sorted(reverted_message_dict["tool_calls"], key=lambda x: x["id"])
+    )
+    assert reverted_message_dict == message
 
 
 @pytest.fixture