diff --git a/libs/partners/openai/langchain_openai/chat_models/base.py b/libs/partners/openai/langchain_openai/chat_models/base.py
index b31742a4e10fb..982979e8949a0 100644
--- a/libs/partners/openai/langchain_openai/chat_models/base.py
+++ b/libs/partners/openai/langchain_openai/chat_models/base.py
@@ -1354,19 +1354,33 @@ def with_structured_output(
             )
         is_pydantic_schema = _is_pydantic_class(schema)
 
-        # Check for Pydantic BaseModel V1
-        if (
-            method == "json_schema"
-            and is_pydantic_schema
-            and issubclass(schema, BaseModelV1)  # type: ignore[arg-type]
-        ):
-            warnings.warn(
-                "Received a Pydantic BaseModel V1 schema. This is not supported by "
-                'method="json_schema". Please use method="function_calling" '
-                "or specify schema via JSON Schema or Pydantic V2 BaseModel. "
-                'Overriding to method="function_calling".'
-            )
-            method = "function_calling"
+        if method == "json_schema":
+            # Check for Pydantic BaseModel V1
+            if (
+                is_pydantic_schema and issubclass(schema, BaseModelV1)  # type: ignore[arg-type]
+            ):
+                warnings.warn(
+                    "Received a Pydantic BaseModel V1 schema. This is not supported by "
+                    'method="json_schema". Please use method="function_calling" '
+                    "or specify schema via JSON Schema or Pydantic V2 BaseModel. "
+                    'Overriding to method="function_calling".'
+                )
+                method = "function_calling"
+            # Check for incompatible model
+            if self.model_name and (
+                self.model_name.startswith("gpt-3")
+                or self.model_name.startswith("gpt-4-")
+                or self.model_name == "gpt-4"
+            ):
+                warnings.warn(
+                    f"Cannot use method='json_schema' with model {self.model_name} "
+                    f"since it doesn't support OpenAI's Structured Output API. You can "
+                    f"see supported models here: "
+                    f"https://platform.openai.com/docs/guides/structured-outputs#supported-models. "  # noqa: E501
+                    "To fix this warning, set `method='function_calling'. "
+                    "Overriding to method='function_calling'."
+                )
+                method = "function_calling"
 
         if method == "function_calling":
             if schema is None:
diff --git a/libs/partners/openai/poetry.lock b/libs/partners/openai/poetry.lock
index 41b8b1e48f15b..04c907494cc81 100644
--- a/libs/partners/openai/poetry.lock
+++ b/libs/partners/openai/poetry.lock
@@ -1,4 +1,4 @@
-# This file is automatically @generated by Poetry 1.8.3 and should not be changed by hand.
+# This file is automatically @generated by Poetry 1.8.5 and should not be changed by hand.
 
 [[package]]
 name = "annotated-types"
@@ -13,13 +13,13 @@ files = [
 
 [[package]]
 name = "anyio"
-version = "4.7.0"
+version = "4.8.0"
 description = "High level compatibility layer for multiple asynchronous event loop implementations"
 optional = false
 python-versions = ">=3.9"
 files = [
-    {file = "anyio-4.7.0-py3-none-any.whl", hash = "sha256:ea60c3723ab42ba6fff7e8ccb0488c898ec538ff4df1f1d5e642c3601d07e352"},
-    {file = "anyio-4.7.0.tar.gz", hash = "sha256:2f834749c602966b7d456a7567cafcb309f96482b5081d14ac93ccd457f9dd48"},
+    {file = "anyio-4.8.0-py3-none-any.whl", hash = "sha256:b5011f270ab5eb0abf13385f851315585cc37ef330dd88e27ec3d34d651fd47a"},
+    {file = "anyio-4.8.0.tar.gz", hash = "sha256:1d9fe889df5212298c0c0723fa20479d1b94883a2df44bd3897aa91083316f7a"},
 ]
 
 [package.dependencies]
@@ -30,7 +30,7 @@ typing_extensions = {version = ">=4.5", markers = "python_version < \"3.13\""}
 
 [package.extras]
 doc = ["Sphinx (>=7.4,<8.0)", "packaging", "sphinx-autodoc-typehints (>=1.2.0)", "sphinx_rtd_theme"]
-test = ["anyio[trio]", "coverage[toml] (>=7)", "exceptiongroup (>=1.2.0)", "hypothesis (>=4.0)", "psutil (>=5.9)", "pytest (>=7.0)", "pytest-mock (>=3.6.1)", "trustme", "truststore (>=0.9.1)", "uvloop (>=0.21)"]
+test = ["anyio[trio]", "coverage[toml] (>=7)", "exceptiongroup (>=1.2.0)", "hypothesis (>=4.0)", "psutil (>=5.9)", "pytest (>=7.0)", "trustme", "truststore (>=0.9.1)", "uvloop (>=0.21)"]
 trio = ["trio (>=0.26.1)"]
 
 [[package]]
@@ -44,129 +44,195 @@ files = [
     {file = "certifi-2024.12.14.tar.gz", hash = "sha256:b650d30f370c2b724812bee08008be0c4163b163ddaec3f2546c1caf65f191db"},
 ]
 
+[[package]]
+name = "cffi"
+version = "1.17.1"
+description = "Foreign Function Interface for Python calling C code."
+optional = false
+python-versions = ">=3.8"
+files = [
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+    {file = "cffi-1.17.1-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:8f2cdc858323644ab277e9bb925ad72ae0e67f69e804f4898c070998d50b1a67"},
+    {file = "cffi-1.17.1-cp310-cp310-manylinux_2_12_i686.manylinux2010_i686.manylinux_2_17_i686.manylinux2014_i686.whl", hash = "sha256:edae79245293e15384b51f88b00613ba9f7198016a5948b5dddf4917d4d26382"},
+    {file = "cffi-1.17.1-cp310-cp310-manylinux_2_17_aarch64.manylinux2014_aarch64.whl", hash = "sha256:45398b671ac6d70e67da8e4224a065cec6a93541bb7aebe1b198a61b58c7b702"},
+    {file = "cffi-1.17.1-cp310-cp310-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl", hash = "sha256:ad9413ccdeda48c5afdae7e4fa2192157e991ff761e7ab8fdd8926f40b160cc3"},
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+
+[package.dependencies]
+pycparser = "*"
+
 [[package]]
 name = "charset-normalizer"
-version = "3.4.0"
+version = "3.4.1"
 description = "The Real First Universal Charset Detector. Open, modern and actively maintained alternative to Chardet."
 optional = false
-python-versions = ">=3.7.0"
+python-versions = ">=3.7"
 files = [
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 ]
 
 [package.dependencies]
@@ -496,7 +562,7 @@ files = [
 
 [[package]]
 name = "langchain-core"
-version = "0.3.30"
+version = "0.3.31"
 description = "Building applications with LLMs through composability"
 optional = false
 python-versions = ">=3.9,<4.0"
@@ -505,7 +571,7 @@ develop = true
 
 [package.dependencies]
 jsonpatch = "^1.33"
-langsmith = ">=0.1.125,<0.3"
+langsmith = ">=0.1.125,<0.4"
 packaging = ">=23.2,<25"
 pydantic = [
     {version = ">=2.5.2,<3.0.0", markers = "python_full_version < \"3.12.4\""},
@@ -521,7 +587,7 @@ url = "../../core"
 
 [[package]]
 name = "langchain-tests"
-version = "0.3.8"
+version = "0.3.9"
 description = "Standard tests for LangChain implementations"
 optional = false
 python-versions = ">=3.9,<4.0"
@@ -530,7 +596,7 @@ develop = true
 
 [package.dependencies]
 httpx = ">=0.25.0,<1"
-langchain-core = "^0.3.22"
+langchain-core = "^0.3.31"
 numpy = [
     {version = ">=1.24.0,<2.0.0", markers = "python_version < \"3.12\""},
     {version = ">=1.26.2,<3", markers = "python_version >= \"3.12\""},
@@ -546,13 +612,13 @@ url = "../../standard-tests"
 
 [[package]]
 name = "langsmith"
-version = "0.2.4"
+version = "0.3.1"
 description = "Client library to connect to the LangSmith LLM Tracing and Evaluation Platform."
 optional = false
 python-versions = "<4.0,>=3.9"
 files = [
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 ]
 
 [package.dependencies]
@@ -564,55 +630,63 @@ pydantic = [
 ]
 requests = ">=2,<3"
 requests-toolbelt = ">=1.0.0,<2.0.0"
+zstandard = ">=0.23.0,<0.24.0"
 
 [package.extras]
 langsmith-pyo3 = ["langsmith-pyo3 (>=0.1.0rc2,<0.2.0)"]
+pytest = ["pytest (>=7.0.0)", "rich (>=13.9.4,<14.0.0)"]
 
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 name = "mypy"
-version = "1.13.0"
+version = "1.14.1"
 description = "Optional static typing for Python"
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 python-versions = ">=3.8"
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+]
+
+[package.dependencies]
+cffi = {version = ">=1.11", markers = "platform_python_implementation == \"PyPy\""}
+
+[package.extras]
+cffi = ["cffi (>=1.11)"]
+
 [metadata]
 lock-version = "2.0"
 python-versions = ">=3.9,<4.0"
-content-hash = "7b96bca67aad51e85bdceb9b491b834bc036aa20da766b999d2c3e2df8e64ae1"
+content-hash = "cdb63207c1dc6597eb2ade4ef0f12e56ac128e7277c9952fa35bc6880b537c9e"
diff --git a/libs/partners/openai/pyproject.toml b/libs/partners/openai/pyproject.toml
index 8f80837ac36f5..3f7a79d9d8426 100644
--- a/libs/partners/openai/pyproject.toml
+++ b/libs/partners/openai/pyproject.toml
@@ -4,7 +4,7 @@ build-backend = "poetry.core.masonry.api"
 
 [tool.poetry]
 name = "langchain-openai"
-version = "0.3.1"
+version = "0.3.2"
 description = "An integration package connecting OpenAI and LangChain"
 authors = []
 readme = "README.md"
@@ -23,7 +23,7 @@ ignore_missing_imports = true
 
 [tool.poetry.dependencies]
 python = ">=3.9,<4.0"
-langchain-core = "^0.3.30"
+langchain-core = "^0.3.31"
 openai = "^1.58.1"
 tiktoken = ">=0.7,<1"
 
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 525020192ba0d..a60d60507e156 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
@@ -27,6 +27,7 @@
     magic_function as invalid_magic_function,
 )
 from pydantic import BaseModel, Field
+from typing_extensions import TypedDict
 
 from langchain_openai import ChatOpenAI
 from tests.unit_tests.fake.callbacks import FakeCallbackHandler
@@ -1220,3 +1221,14 @@ def test_o1_doesnt_stream() -> None:
 def test_o1_stream_default_works() -> None:
     result = list(ChatOpenAI(model="o1").stream("say 'hi'"))
     assert len(result) > 0
+
+
+def test_structured_output_old_model() -> None:
+    class Output(TypedDict):
+        """output."""
+
+        foo: str
+
+    llm = ChatOpenAI(model="gpt-4").with_structured_output(Output)
+    output = llm.invoke("bar")
+    assert "foo" in output
diff --git a/libs/partners/openai/tests/unit_tests/chat_models/test_azure.py b/libs/partners/openai/tests/unit_tests/chat_models/test_azure.py
index b57768c8ba003..bee3f742a5efe 100644
--- a/libs/partners/openai/tests/unit_tests/chat_models/test_azure.py
+++ b/libs/partners/openai/tests/unit_tests/chat_models/test_azure.py
@@ -3,6 +3,9 @@
 import os
 from unittest import mock
 
+import pytest
+from typing_extensions import TypedDict
+
 from langchain_openai import AzureChatOpenAI
 
 
@@ -59,3 +62,22 @@ def test_initialize_azure_openai_with_openai_api_base_set() -> None:
         ls_params = llm._get_ls_params()
         assert ls_params["ls_provider"] == "azure"
         assert ls_params["ls_model_name"] == "35-turbo-dev"
+
+
+def test_structured_output_old_model() -> None:
+    class Output(TypedDict):
+        """output."""
+
+        foo: str
+
+    with pytest.warns(match="Cannot use method='json_schema'"):
+        llm = AzureChatOpenAI(  # type: ignore[call-arg]
+            model="gpt-35-turbo",
+            azure_deployment="35-turbo-dev",
+            openai_api_version="2023-05-15",
+            azure_endpoint="my-base-url",
+        ).with_structured_output(Output)
+
+    # assert tool calling was used instead of json_schema
+    assert "tools" in llm.steps[0].kwargs  # type: ignore
+    assert "response_format" not in llm.steps[0].kwargs  # type: ignore
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 5eac32c0447dd..a7b3e5f102ee8 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
@@ -746,7 +746,7 @@ class Foo(BaseModel):
 def test_schema_from_with_structured_output(schema: Type) -> None:
     """Test schema from with_structured_output."""
 
-    llm = ChatOpenAI()
+    llm = ChatOpenAI(model="gpt-4o")
 
     structured_llm = llm.with_structured_output(
         schema, method="json_schema", strict=True
@@ -886,3 +886,16 @@ def test_init_o1() -> None:
     with pytest.warns(None) as record:  # type: ignore[call-overload]
         ChatOpenAI(model="o1", reasoning_effort="medium")
     assert len(record) == 0
+
+
+def test_structured_output_old_model() -> None:
+    class Output(TypedDict):
+        """output."""
+
+        foo: str
+
+    with pytest.warns(match="Cannot use method='json_schema'"):
+        llm = ChatOpenAI(model="gpt-4").with_structured_output(Output)
+    # assert tool calling was used instead of json_schema
+    assert "tools" in llm.steps[0].kwargs  # type: ignore
+    assert "response_format" not in llm.steps[0].kwargs  # type: ignore