diff --git a/llama-index-integrations/llms/llama-index-llms-openai/llama_index/llms/openai/utils.py b/llama-index-integrations/llms/llama-index-llms-openai/llama_index/llms/openai/utils.py
index 6e48083d24960..220ad8d860ccb 100644
--- a/llama-index-integrations/llms/llama-index-llms-openai/llama_index/llms/openai/utils.py
+++ b/llama-index-integrations/llms/llama-index-llms-openai/llama_index/llms/openai/utils.py
@@ -2,7 +2,13 @@
 import os
 from typing import Any, Callable, Dict, List, Optional, Sequence, Tuple, Type, Union
 
+import openai
 from deprecated import deprecated
+from openai.types.chat import ChatCompletionMessageParam, ChatCompletionMessageToolCall
+from openai.types.chat.chat_completion_chunk import ChoiceDeltaToolCall
+from openai.types.chat.chat_completion_message import ChatCompletionMessage
+from openai.types.chat.chat_completion_token_logprob import ChatCompletionTokenLogprob
+from openai.types.completion_choice import Logprobs
 from tenacity import (
     before_sleep_log,
     retry,
@@ -14,20 +20,15 @@
 )
 from tenacity.stop import stop_base
 
-import openai
 from llama_index.core.base.llms.generic_utils import get_from_param_or_env
 from llama_index.core.base.llms.types import (
     ChatMessage,
     ImageBlock,
     LogProb,
+    MessageRole,
     TextBlock,
 )
 from llama_index.core.bridge.pydantic import BaseModel
-from openai.types.chat import ChatCompletionMessageParam, ChatCompletionMessageToolCall
-from openai.types.chat.chat_completion_chunk import ChoiceDeltaToolCall
-from openai.types.chat.chat_completion_message import ChatCompletionMessage
-from openai.types.chat.chat_completion_token_logprob import ChatCompletionTokenLogprob
-from openai.types.completion_choice import Logprobs
 
 DEFAULT_OPENAI_API_TYPE = "open_ai"
 DEFAULT_OPENAI_API_BASE = "https://api.openai.com/v1"
@@ -292,9 +293,14 @@ def to_openai_message_dict(
             msg = f"Unsupported content block type: {type(block).__name__}"
             raise ValueError(msg)
 
-    # NOTE: Sending a blank string to openai will cause an error.
-    # This will commonly happen with tool calls.
-    content_txt = None if content_txt == "" else content_txt
+    # NOTE: Sending a null value (None) for Tool Message to OpenAI will cause error
+    # It's only Allowed to send None if it's an Assistant Message
+    # Reference: https://platform.openai.com/docs/api-reference/chat/create
+    content_txt = (
+        None
+        if content_txt == "" and message.role == MessageRole.ASSISTANT
+        else content_txt
+    )
 
     # NOTE: Despite what the openai docs say, if the role is ASSISTANT, SYSTEM
     # or TOOL, 'content' cannot be a list and must be string instead.
@@ -302,10 +308,12 @@ def to_openai_message_dict(
     # as the content. This will avoid breaking openai-like APIs.
     message_dict = {
         "role": message.role.value,
-        "content": content_txt
-        if message.role.value in ("assistant", "tool", "system")
-        or all(isinstance(block, TextBlock) for block in message.blocks)
-        else content,
+        "content": (
+            content_txt
+            if message.role.value in ("assistant", "tool", "system")
+            or all(isinstance(block, TextBlock) for block in message.blocks)
+            else content
+        ),
     }
 
     # TODO: O1 models do not support system prompts
diff --git a/llama-index-integrations/llms/llama-index-llms-openai/pyproject.toml b/llama-index-integrations/llms/llama-index-llms-openai/pyproject.toml
index efd26805d9b51..e92a58e044b7d 100644
--- a/llama-index-integrations/llms/llama-index-llms-openai/pyproject.toml
+++ b/llama-index-integrations/llms/llama-index-llms-openai/pyproject.toml
@@ -29,7 +29,7 @@ exclude = ["**/BUILD"]
 license = "MIT"
 name = "llama-index-llms-openai"
 readme = "README.md"
-version = "0.3.13"
+version = "0.3.14"
 
 [tool.poetry.dependencies]
 python = ">=3.9,<4.0"
diff --git a/llama-index-integrations/llms/llama-index-llms-openai/tests/test_openai_utils.py b/llama-index-integrations/llms/llama-index-llms-openai/tests/test_openai_utils.py
index 9f7ec48c5e923..b829d30b1dcb5 100644
--- a/llama-index-integrations/llms/llama-index-llms-openai/tests/test_openai_utils.py
+++ b/llama-index-integrations/llms/llama-index-llms-openai/tests/test_openai_utils.py
@@ -59,7 +59,7 @@ def chat_messages_with_function_calling() -> List[ChatMessage]:
 
 
 @pytest.fixture()
-def openi_message_dicts_with_function_calling() -> List[ChatCompletionMessageParam]:
+def openai_message_dicts_with_function_calling() -> List[ChatCompletionMessageParam]:
     return [
         {
             "role": "user",
@@ -158,19 +158,19 @@ def test_to_openai_message_dicts_basic_string() -> None:
 
 def test_to_openai_message_dicts_function_calling(
     chat_messages_with_function_calling: List[ChatMessage],
-    openi_message_dicts_with_function_calling: List[ChatCompletionMessageParam],
+    openai_message_dicts_with_function_calling: List[ChatCompletionMessageParam],
 ) -> None:
     message_dicts = to_openai_message_dicts(
         chat_messages_with_function_calling,
     )
-    assert message_dicts == openi_message_dicts_with_function_calling
+    assert message_dicts == openai_message_dicts_with_function_calling
 
 
 def test_from_openai_message_dicts_function_calling(
-    openi_message_dicts_with_function_calling: List[ChatCompletionMessageParam],
+    openai_message_dicts_with_function_calling: List[ChatCompletionMessageParam],
     chat_messages_with_function_calling: List[ChatMessage],
 ) -> None:
-    chat_messages = from_openai_message_dicts(openi_message_dicts_with_function_calling)  # type: ignore
+    chat_messages = from_openai_message_dicts(openai_message_dicts_with_function_calling)  # type: ignore
 
     # assert attributes match
     for chat_message, chat_message_with_function_calling in zip(