From 7a4c1fcf847a79e5f1f448716c8bbc78c6b76513 Mon Sep 17 00:00:00 2001
From: Chester Curme <chester.curme@gmail.com>
Date: Wed, 18 Jun 2025 09:53:53 -0400
Subject: [PATCH 1/4] bump langchain-tests

---
 libs/genai/poetry.lock    | 759 +++++++++++++++++++++++++++++++++++++-
 libs/genai/pyproject.toml |   6 +-
 2 files changed, 744 insertions(+), 21 deletions(-)

diff --git a/libs/genai/poetry.lock b/libs/genai/poetry.lock
index 328b363f3..9d3c14400 100644
--- a/libs/genai/poetry.lock
+++ b/libs/genai/poetry.lock
@@ -66,7 +66,6 @@ description = "Foreign Function Interface for Python calling C code."
 optional = false
 python-versions = ">=3.8"
 groups = ["main", "test"]
-markers = "platform_python_implementation == \"PyPy\""
 files = [
     {file = "cffi-1.17.1-cp310-cp310-macosx_10_9_x86_64.whl", hash = "sha256:df8b1c11f177bc2313ec4b2d46baec87a5f3e71fc8b45dab2ee7cae86d9aba14"},
     {file = "cffi-1.17.1-cp310-cp310-macosx_11_0_arm64.whl", hash = "sha256:8f2cdc858323644ab277e9bb925ad72ae0e67f69e804f4898c070998d50b1a67"},
@@ -136,6 +135,7 @@ files = [
     {file = "cffi-1.17.1-cp39-cp39-win_amd64.whl", hash = "sha256:d016c76bdd850f3c626af19b0542c9677ba156e4ee4fccfdd7848803533ef662"},
     {file = "cffi-1.17.1.tar.gz", hash = "sha256:1c39c6016c32bc48dd54561950ebd6836e1670f2ae46128f67cf49e789c52824"},
 ]
+markers = {main = "platform_python_implementation == \"PyPy\""}
 
 [package.dependencies]
 pycparser = "*"
@@ -575,6 +575,31 @@ files = [
 [package.extras]
 all = ["flake8 (>=7.1.1)", "mypy (>=1.11.2)", "pytest (>=8.3.2)", "ruff (>=0.6.2)"]
 
+[[package]]
+name = "importlib-metadata"
+version = "8.7.0"
+description = "Read metadata from Python packages"
+optional = false
+python-versions = ">=3.9"
+groups = ["test"]
+markers = "python_version == \"3.9\""
+files = [
+    {file = "importlib_metadata-8.7.0-py3-none-any.whl", hash = "sha256:e5dd1551894c77868a30651cef00984d50e1002d06942a7101d34870c5f02afd"},
+    {file = "importlib_metadata-8.7.0.tar.gz", hash = "sha256:d13b81ad223b890aa16c5471f2ac3056cf76c5f10f82d6f9292f0b415f389000"},
+]
+
+[package.dependencies]
+zipp = ">=3.20"
+
+[package.extras]
+check = ["pytest-checkdocs (>=2.4)", "pytest-ruff (>=0.2.1) ; sys_platform != \"cygwin\""]
+cover = ["pytest-cov"]
+doc = ["furo", "jaraco.packaging (>=9.3)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-lint"]
+enabler = ["pytest-enabler (>=2.2)"]
+perf = ["ipython"]
+test = ["flufl.flake8", "importlib_resources (>=1.3) ; python_version < \"3.9\"", "jaraco.test (>=5.4)", "packaging", "pyfakefs", "pytest (>=6,!=8.1.*)", "pytest-perf (>=0.9.2)"]
+type = ["pytest-mypy"]
+
 [[package]]
 name = "iniconfig"
 version = "2.0.0"
@@ -616,19 +641,19 @@ files = [
 
 [[package]]
 name = "langchain-core"
-version = "0.3.62"
+version = "0.3.65"
 description = "Building applications with LLMs through composability"
 optional = false
 python-versions = ">=3.9"
 groups = ["main", "test"]
 files = [
-    {file = "langchain_core-0.3.62-py3-none-any.whl", hash = "sha256:242cef42be32baa5c7cd03df719d21093323b5271fff9efbe0ca9a0dfa8ee2bf"},
-    {file = "langchain_core-0.3.62.tar.gz", hash = "sha256:e75e483b0b602a2fdcfbe349be7efb7f1c1c04b20f8d51c7892e78fbecc8a823"},
+    {file = "langchain_core-0.3.65-py3-none-any.whl", hash = "sha256:80e8faf6e9f331f8ef728f3fe793549f1d3fb244fcf9e1bdcecab6a6f4669394"},
+    {file = "langchain_core-0.3.65.tar.gz", hash = "sha256:54b5e0c8d9bb405415c3211da508ef9cfe0acbe5b490d1b4a15664408ee82d9b"},
 ]
 
 [package.dependencies]
 jsonpatch = ">=1.33,<2.0"
-langsmith = ">=0.1.126,<0.4"
+langsmith = ">=0.3.45,<0.4"
 packaging = ">=23.2,<25"
 pydantic = ">=2.7.4"
 PyYAML = ">=5.3"
@@ -637,43 +662,48 @@ typing-extensions = ">=4.7"
 
 [[package]]
 name = "langchain-tests"
-version = "0.3.19"
+version = "0.3.20"
 description = "Standard tests for LangChain implementations"
 optional = false
-python-versions = "<4.0,>=3.9"
+python-versions = ">=3.9"
 groups = ["test"]
 files = [
-    {file = "langchain_tests-0.3.19-py3-none-any.whl", hash = "sha256:f235b74421e9bf71e9453405287204a4e11f20ed3829f9b7eee9ef55df47a50a"},
-    {file = "langchain_tests-0.3.19.tar.gz", hash = "sha256:0d835148fdea7a5bcb3e26c7128b110bb4fa9532b070993566d107632a26b3a0"},
+    {file = "langchain_tests-0.3.20-py3-none-any.whl", hash = "sha256:6cc7ae64eb8dea65360a968840abe8d947c5382b95e065431c9dd061ee1dacd8"},
+    {file = "langchain_tests-0.3.20.tar.gz", hash = "sha256:b94c05e37d191d4768a1a5064f2ca4053bacd48ff41e10af245ffa6a065ead4d"},
 ]
 
 [package.dependencies]
 httpx = ">=0.25.0,<1"
-langchain-core = ">=0.3.53,<1.0.0"
+langchain-core = ">=0.3.63,<1.0.0"
 numpy = [
     {version = ">=1.26.2", markers = "python_version < \"3.13\""},
     {version = ">=2.1.0", markers = "python_version >= \"3.13\""},
 ]
 pytest = ">=7,<9"
 pytest-asyncio = ">=0.20,<1"
+pytest-benchmark = "*"
+pytest-codspeed = "*"
+pytest-recording = "*"
 pytest-socket = ">=0.6.0,<1"
 syrupy = ">=4,<5"
+vcrpy = ">=7.0"
 
 [[package]]
 name = "langsmith"
-version = "0.3.9"
+version = "0.3.45"
 description = "Client library to connect to the LangSmith LLM Tracing and Evaluation Platform."
 optional = false
-python-versions = "<4.0,>=3.9"
+python-versions = ">=3.9"
 groups = ["main", "test"]
 files = [
-    {file = "langsmith-0.3.9-py3-none-any.whl", hash = "sha256:0e250cca50d1142d8bb00528da573c83bef1c41d78de43b2c032f8d11a308d04"},
-    {file = "langsmith-0.3.9.tar.gz", hash = "sha256:460e70d349282cf8d7d503cdf16684db58061d12a6a512daf626257a3218e0fb"},
+    {file = "langsmith-0.3.45-py3-none-any.whl", hash = "sha256:5b55f0518601fa65f3bb6b1a3100379a96aa7b3ed5e9380581615ba9c65ed8ed"},
+    {file = "langsmith-0.3.45.tar.gz", hash = "sha256:1df3c6820c73ed210b2c7bc5cdb7bfa19ddc9126cd03fdf0da54e2e171e6094d"},
 ]
 
 [package.dependencies]
 httpx = ">=0.23.0,<1"
 orjson = {version = ">=3.9.14,<4.0.0", markers = "platform_python_implementation != \"PyPy\""}
+packaging = ">=23.2"
 pydantic = [
     {version = ">=1,<3", markers = "python_full_version < \"3.12.4\""},
     {version = ">=2.7.4,<3.0.0", markers = "python_full_version >= \"3.12.4\""},
@@ -684,8 +714,170 @@ zstandard = ">=0.23.0,<0.24.0"
 
 [package.extras]
 langsmith-pyo3 = ["langsmith-pyo3 (>=0.1.0rc2,<0.2.0)"]
+openai-agents = ["openai-agents (>=0.0.3,<0.1)"]
+otel = ["opentelemetry-api (>=1.30.0,<2.0.0)", "opentelemetry-exporter-otlp-proto-http (>=1.30.0,<2.0.0)", "opentelemetry-sdk (>=1.30.0,<2.0.0)"]
 pytest = ["pytest (>=7.0.0)", "rich (>=13.9.4,<14.0.0)"]
 
+[[package]]
+name = "markdown-it-py"
+version = "3.0.0"
+description = "Python port of markdown-it. Markdown parsing, done right!"
+optional = false
+python-versions = ">=3.8"
+groups = ["test"]
+files = [
+    {file = "markdown-it-py-3.0.0.tar.gz", hash = "sha256:e3f60a94fa066dc52ec76661e37c851cb232d92f9886b15cb560aaada2df8feb"},
+    {file = "markdown_it_py-3.0.0-py3-none-any.whl", hash = "sha256:355216845c60bd96232cd8d8c40e8f9765cc86f46880e43a8fd22dc1a1a8cab1"},
+]
+
+[package.dependencies]
+mdurl = ">=0.1,<1.0"
+
+[package.extras]
+benchmarking = ["psutil", "pytest", "pytest-benchmark"]
+code-style = ["pre-commit (>=3.0,<4.0)"]
+compare = ["commonmark (>=0.9,<1.0)", "markdown (>=3.4,<4.0)", "mistletoe (>=1.0,<2.0)", "mistune (>=2.0,<3.0)", "panflute (>=2.3,<3.0)"]
+linkify = ["linkify-it-py (>=1,<3)"]
+plugins = ["mdit-py-plugins"]
+profiling = ["gprof2dot"]
+rtd = ["jupyter_sphinx", "mdit-py-plugins", "myst-parser", "pyyaml", "sphinx", "sphinx-copybutton", "sphinx-design", "sphinx_book_theme"]
+testing = ["coverage", "pytest", "pytest-cov", "pytest-regressions"]
+
+[[package]]
+name = "mdurl"
+version = "0.1.2"
+description = "Markdown URL utilities"
+optional = false
+python-versions = ">=3.7"
+groups = ["test"]
+files = [
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+
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+name = "multidict"
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+groups = ["test"]
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 [[package]]
 name = "mypy"
 version = "1.15.0"
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 optional = false
 python-versions = ">=3.9"
 groups = ["test", "typing"]
-markers = "python_version < \"3.11\""
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 groups = ["test", "typing"]
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 testing = ["pytest", "pytest-benchmark"]
 
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+
 [[package]]
 name = "proto-plus"
 version = "1.26.0"
@@ -1022,6 +1322,18 @@ files = [
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 ]
 
+[[package]]
+name = "py-cpuinfo"
+version = "9.0.0"
+description = "Get CPU info with pure Python"
+optional = false
+python-versions = "*"
+groups = ["test"]
+files = [
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+]
+
 [[package]]
 name = "pyasn1"
 version = "0.6.1"
@@ -1056,11 +1368,11 @@ description = "C parser in Python"
 optional = false
 python-versions = ">=3.8"
 groups = ["main", "test"]
-markers = "platform_python_implementation == \"PyPy\""
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 ]
+markers = {main = "platform_python_implementation == \"PyPy\""}
 
 [[package]]
 name = "pydantic"
@@ -1196,6 +1508,21 @@ files = [
 [package.dependencies]
 typing-extensions = ">=4.6.0,<4.7.0 || >4.7.0"
 
+[[package]]
+name = "pygments"
+version = "2.19.1"
+description = "Pygments is a syntax highlighting package written in Python."
+optional = false
+python-versions = ">=3.8"
+groups = ["test"]
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+]
+
+[package.extras]
+windows-terminal = ["colorama (>=0.4.6)"]
+
 [[package]]
 name = "pytest"
 version = "7.4.4"
@@ -1238,6 +1565,60 @@ pytest = ">=7.0.0"
 docs = ["sphinx (>=5.3)", "sphinx-rtd-theme (>=1.0)"]
 testing = ["coverage (>=6.2)", "flaky (>=3.5.0)", "hypothesis (>=5.7.1)", "mypy (>=0.931)", "pytest-trio (>=0.7.0)"]
 
+[[package]]
+name = "pytest-benchmark"
+version = "5.0.1"
+description = "A ``pytest`` fixture for benchmarking code. It will group the tests into rounds that are calibrated to the chosen timer."
+optional = false
+python-versions = ">=3.9"
+groups = ["test"]
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+
 [[package]]
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 version = "3.14.0"
@@ -1256,6 +1637,26 @@ pytest = ">=6.2.5"
 [package.extras]
 dev = ["pre-commit", "pytest-asyncio", "tox"]
 
+[[package]]
+name = "pytest-recording"
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+description = "A pytest plugin powered by VCR.py to record and replay HTTP traffic"
+optional = false
+python-versions = ">=3.9"
+groups = ["test"]
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+
+[package.extras]
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+tests = ["pytest-httpbin", "pytest-mock", "requests", "werkzeug (==3.1.3)"]
+
 [[package]]
 name = "pytest-retry"
 version = "1.7.0"
@@ -1420,6 +1821,26 @@ files = [
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 requests = ">=2.0.1,<3.0.0"
 
+[[package]]
+name = "rich"
+version = "14.0.0"
+description = "Render rich text, tables, progress bars, syntax highlighting, markdown and more to the terminal"
+optional = false
+python-versions = ">=3.8.0"
+groups = ["test"]
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+
+[package.extras]
+jupyter = ["ipywidgets (>=7.5.1,<9)"]
+
 [[package]]
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 version = "4.9"
@@ -1584,6 +2005,22 @@ files = [
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+python-versions = ">=3.7"
+groups = ["dev", "typing"]
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+files = [
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+[package.dependencies]
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 version = "2.32.0.20241016"
@@ -1591,6 +2028,7 @@ description = "Typing stubs for requests"
 optional = false
 python-versions = ">=3.8"
 groups = ["dev", "typing"]
+markers = "platform_python_implementation != \"PyPy\" and python_version >= \"3.10\""
 files = [
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@@ -1599,6 +2037,19 @@ files = [
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+python-versions = "*"
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+markers = "platform_python_implementation == \"PyPy\" or python_version == \"3.9\""
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+
 [[package]]
 name = "urllib3"
 version = "2.3.0"
@@ -1618,6 +2087,7 @@ description = "HTTP library with thread-safe connection pooling, file post, and
 optional = false
 python-versions = ">=3.9"
 groups = ["main", "dev", "test", "typing"]
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 zstd = ["zstandard (>=0.18.0)"]
 
+[[package]]
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+description = "Automatically mock your HTTP interactions to simplify and speed up testing"
+optional = false
+python-versions = ">=3.9"
+groups = ["test"]
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+[package.dependencies]
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+urllib3 = [
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+    {version = "*", markers = "platform_python_implementation != \"PyPy\" and python_version >= \"3.10\""},
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+
+[package.extras]
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+
 [[package]]
 name = "watchdog"
 version = "6.0.0"
@@ -1672,6 +2166,235 @@ files = [
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 watchmedo = ["PyYAML (>=3.10)"]
 
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+    {file = "yarl-1.20.1.tar.gz", hash = "sha256:d017a4997ee50c91fd5466cef416231bb82177b93b029906cefc542ce14c35ac"},
+]
+
+[package.dependencies]
+idna = ">=2.0"
+multidict = ">=4.0"
+propcache = ">=0.2.1"
+
+[[package]]
+name = "zipp"
+version = "3.23.0"
+description = "Backport of pathlib-compatible object wrapper for zip files"
+optional = false
+python-versions = ">=3.9"
+groups = ["test"]
+markers = "python_version == \"3.9\""
+files = [
+    {file = "zipp-3.23.0-py3-none-any.whl", hash = "sha256:071652d6115ed432f5ce1d34c336c0adfd6a884660d1e9712a256d3d3bd4b14e"},
+    {file = "zipp-3.23.0.tar.gz", hash = "sha256:a07157588a12518c9d4034df3fbbee09c814741a33ff63c05fa29d26a2404166"},
+]
+
+[package.extras]
+check = ["pytest-checkdocs (>=2.4)", "pytest-ruff (>=0.2.1) ; sys_platform != \"cygwin\""]
+cover = ["pytest-cov"]
+doc = ["furo", "jaraco.packaging (>=9.3)", "jaraco.tidelift (>=1.4)", "rst.linker (>=1.9)", "sphinx (>=3.5)", "sphinx-lint"]
+enabler = ["pytest-enabler (>=2.2)"]
+test = ["big-O", "jaraco.functools", "jaraco.itertools", "jaraco.test", "more_itertools", "pytest (>=6,!=8.1.*)", "pytest-ignore-flaky"]
+type = ["pytest-mypy"]
+
 [[package]]
 name = "zstandard"
 version = "0.23.0"
@@ -1788,4 +2511,4 @@ cffi = ["cffi (>=1.11)"]
 [metadata]
 lock-version = "2.1"
 python-versions = ">=3.9,<4.0"
-content-hash = "84a4702836774f32920d1304e6ead667db1d0edd91777a9f609a2ba36bbdb8da"
+content-hash = "9af08fd2cdb3bf805c056add03a0559ebd93e42321d0ee2011032fadf65be211"
diff --git a/libs/genai/pyproject.toml b/libs/genai/pyproject.toml
index 8060abc40..12eda088f 100644
--- a/libs/genai/pyproject.toml
+++ b/libs/genai/pyproject.toml
@@ -29,7 +29,7 @@ pytest-watcher = "^0.3.4"
 pytest-asyncio = "^0.21.1"
 pytest-retry = "^1.7.0"
 numpy = ">=1.26.2"
-langchain-tests = "0.3.19"
+langchain-tests = "0.3.20"
 
 [tool.codespell]
 ignore-words-list = "rouge"
@@ -58,7 +58,7 @@ ruff = "^0.1.5"
 
 [tool.poetry.group.typing.dependencies]
 mypy = "^1.10"
-types-requests = "^2.28.11.5"
+types-requests = "^2.31.0"
 types-google-cloud-ndb = "^2.2.0.1"
 types-protobuf = "^4.24.0.20240302"
 numpy = ">=1.26.2"
@@ -68,7 +68,7 @@ numpy = ">=1.26.2"
 optional = true
 
 [tool.poetry.group.dev.dependencies]
-types-requests = "^2.31.0.10"
+types-requests = "^2.31.0"
 types-google-cloud-ndb = "^2.2.0.1"
 
 [tool.ruff.lint]

From 7d18f4db344a9bfed192e86c3f74cba7e62e68c5 Mon Sep 17 00:00:00 2001
From: Chester Curme <chester.curme@gmail.com>
Date: Wed, 18 Jun 2025 10:22:44 -0400
Subject: [PATCH 2/4] cache sync client

---
 .../langchain_google_genai/_client_utils.py   | 30 +++++++++++++++++++
 .../langchain_google_genai/chat_models.py     | 24 ++++++++++-----
 2 files changed, 47 insertions(+), 7 deletions(-)
 create mode 100644 libs/genai/langchain_google_genai/_client_utils.py

diff --git a/libs/genai/langchain_google_genai/_client_utils.py b/libs/genai/langchain_google_genai/_client_utils.py
new file mode 100644
index 000000000..3866b0325
--- /dev/null
+++ b/libs/genai/langchain_google_genai/_client_utils.py
@@ -0,0 +1,30 @@
+import asyncio
+from functools import lru_cache
+from typing import Any, Literal, Optional, Union
+from weakref import WeakKeyDictionary
+
+from google.ai.generativelanguage_v1beta import (
+    GenerativeServiceClient as v1betaGenerativeServiceClient,
+)
+
+from langchain_google_genai._common import get_client_info
+
+from . import _genai_extension as genaix
+
+
+# Cache sync client
+@lru_cache
+def _get_sync_client(
+    *,
+    api_key: Optional[str],
+    model: str,
+    transport: str,
+) -> v1betaGenerativeServiceClient:
+    """Return a shared sync client."""
+    client_info = get_client_info(f"ChatGoogleGenerativeAI:{model}")
+    return genaix.build_generative_service(
+        api_key=api_key,
+        client_info=client_info,
+        client_options=None,
+        transport=transport,
+    )
diff --git a/libs/genai/langchain_google_genai/chat_models.py b/libs/genai/langchain_google_genai/chat_models.py
index de8141741..d77a3cad4 100644
--- a/libs/genai/langchain_google_genai/chat_models.py
+++ b/libs/genai/langchain_google_genai/chat_models.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
 import asyncio
+import atexit
 import base64
 import io
 import json
@@ -99,6 +100,7 @@
 )
 from typing_extensions import Self, is_typeddict
 
+from langchain_google_genai._client_utils import _get_sync_client
 from langchain_google_genai._common import (
     GoogleGenerativeAIError,
     SafetySettingDict,
@@ -1164,14 +1166,22 @@ def validate_environment(self) -> Self:
             else:
                 google_api_key = self.google_api_key
         transport: Optional[str] = self.transport
-        self.client = genaix.build_generative_service(
-            credentials=self.credentials,
-            api_key=google_api_key,
-            client_info=client_info,
-            client_options=self.client_options,
-            transport=transport,
-        )
+        if self.client_options is None and self.credentials is None:
+            self.client = _get_sync_client(
+                api_key=google_api_key,
+                model=self.model,
+                transport=transport,
+            )
+        else:
+            self.client = genaix.build_generative_service(
+                credentials=self.credentials,
+                api_key=google_api_key,
+                client_info=get_client_info(f"ChatGoogleGenerativeAI:{self.model}"),
+                client_options=self.client_options,
+                transport=transport,
+            )
         self.async_client_running = None
+        atexit.register(self.client.transport.close)
         return self
 
     @property

From b91cccf62bd6bef644f4cfe291cb44e8509532c5 Mon Sep 17 00:00:00 2001
From: Chester Curme <chester.curme@gmail.com>
Date: Wed, 18 Jun 2025 11:39:22 -0400
Subject: [PATCH 3/4] cache async client (cleanup issue)

---
 .../langchain_google_genai/_client_utils.py   | 62 ++++++++++++++++++-
 .../langchain_google_genai/chat_models.py     | 29 ++++-----
 2 files changed, 76 insertions(+), 15 deletions(-)

diff --git a/libs/genai/langchain_google_genai/_client_utils.py b/libs/genai/langchain_google_genai/_client_utils.py
index 3866b0325..6965af638 100644
--- a/libs/genai/langchain_google_genai/_client_utils.py
+++ b/libs/genai/langchain_google_genai/_client_utils.py
@@ -1,8 +1,11 @@
 import asyncio
 from functools import lru_cache
-from typing import Any, Literal, Optional, Union
+from typing import Optional
 from weakref import WeakKeyDictionary
 
+from google.ai.generativelanguage_v1beta import (
+    GenerativeServiceAsyncClient as v1betaGenerativeServiceAsyncClient,
+)
 from google.ai.generativelanguage_v1beta import (
     GenerativeServiceClient as v1betaGenerativeServiceClient,
 )
@@ -28,3 +31,60 @@ def _get_sync_client(
         client_options=None,
         transport=transport,
     )
+
+
+# Cache async client - must store caches per event loop
+_client_caches: WeakKeyDictionary = WeakKeyDictionary()
+
+
+def _create_async_client(
+    *,
+    api_key: Optional[str],
+    model: str,
+    transport: Optional[str],
+) -> v1betaGenerativeServiceAsyncClient:
+    """Create a new async client."""
+    # async clients don't support "rest" transport
+    # https://github.com/googleapis/gapic-generator-python/issues/1962
+    if transport == "rest":
+        transport = "grpc_asyncio"
+    return genaix.build_generative_async_service(
+        credentials=None,
+        api_key=api_key,
+        client_info=get_client_info(f"ChatGoogleGenerativeAI:{model}"),
+        client_options=None,
+        transport=transport,
+    )
+
+
+def _get_async_client(
+    *,
+    api_key: Optional[str],
+    model: str,
+    transport: Optional[str],
+) -> v1betaGenerativeServiceAsyncClient:
+    """Return a shared async client per event loop."""
+    try:
+        loop = asyncio.get_running_loop()
+    except RuntimeError:
+        # If no event loop is running, don't cache
+        return _create_async_client(
+            api_key=api_key,
+            model=model,
+            transport=transport,
+        )
+
+    # Get or create cache for this event loop
+    if loop not in _client_caches:
+        _client_caches[loop] = {}
+
+    cache_key = (api_key, model, transport)
+
+    if cache_key not in _client_caches[loop]:
+        _client_caches[loop][cache_key] = _create_async_client(
+            api_key=api_key,
+            model=model,
+            transport=transport,
+        )
+
+    return _client_caches[loop][cache_key]
diff --git a/libs/genai/langchain_google_genai/chat_models.py b/libs/genai/langchain_google_genai/chat_models.py
index d77a3cad4..90f761741 100644
--- a/libs/genai/langchain_google_genai/chat_models.py
+++ b/libs/genai/langchain_google_genai/chat_models.py
@@ -100,7 +100,7 @@
 )
 from typing_extensions import Self, is_typeddict
 
-from langchain_google_genai._client_utils import _get_sync_client
+from langchain_google_genai._client_utils import _get_async_client, _get_sync_client
 from langchain_google_genai._common import (
     GoogleGenerativeAIError,
     SafetySettingDict,
@@ -1158,7 +1158,6 @@ def validate_environment(self) -> Self:
 
         additional_headers = self.additional_headers or {}
         self.default_metadata = tuple(additional_headers.items())
-        client_info = get_client_info(f"ChatGoogleGenerativeAI:{self.model}")
         google_api_key = None
         if not self.credentials:
             if isinstance(self.google_api_key, SecretStr):
@@ -1198,18 +1197,20 @@ def async_client(self) -> v1betaGenerativeServiceAsyncClient:
         # this check ensures that async client is only initialized
         # within an asyncio event loop to avoid the error
         if not self.async_client_running and _is_event_loop_running():
-            # async clients don't support "rest" transport
-            # https://github.com/googleapis/gapic-generator-python/issues/1962
-            transport = self.transport
-            if transport == "rest":
-                transport = "grpc_asyncio"
-            self.async_client_running = genaix.build_generative_async_service(
-                credentials=self.credentials,
-                api_key=google_api_key,
-                client_info=get_client_info(f"ChatGoogleGenerativeAI:{self.model}"),
-                client_options=self.client_options,
-                transport=transport,
-            )
+            if self.credentials is None and self.client_options is None:
+                self.async_client_running = _get_async_client(
+                    api_key=google_api_key,
+                    model=self.model,
+                    transport=self.transport,
+                )
+            else:
+                self.async_client_running = genaix.build_generative_async_service(
+                    credentials=self.credentials,
+                    api_key=google_api_key,
+                    client_info=get_client_info(f"ChatGoogleGenerativeAI:{self.model}"),
+                    client_options=self.client_options,
+                    transport=self.transport,
+                )
         return self.async_client_running
 
     @property

From 464a6a7155c4cf9d6d3207ebbafb390bd14e3219 Mon Sep 17 00:00:00 2001
From: Chester Curme <chester.curme@gmail.com>
Date: Wed, 18 Jun 2025 11:40:21 -0400
Subject: [PATCH 4/4] (wip) attempt to fix cleanup issue

---
 .../langchain_google_genai/_client_utils.py   | 31 +++++++++++++++++--
 .../langchain_google_genai/chat_models.py     | 15 +++++++++
 2 files changed, 44 insertions(+), 2 deletions(-)

diff --git a/libs/genai/langchain_google_genai/_client_utils.py b/libs/genai/langchain_google_genai/_client_utils.py
index 6965af638..40e934690 100644
--- a/libs/genai/langchain_google_genai/_client_utils.py
+++ b/libs/genai/langchain_google_genai/_client_utils.py
@@ -1,7 +1,7 @@
 import asyncio
 from functools import lru_cache
 from typing import Optional
-from weakref import WeakKeyDictionary
+from weakref import WeakKeyDictionary, WeakSet
 
 from google.ai.generativelanguage_v1beta import (
     GenerativeServiceAsyncClient as v1betaGenerativeServiceAsyncClient,
@@ -35,6 +35,7 @@ def _get_sync_client(
 
 # Cache async client - must store caches per event loop
 _client_caches: WeakKeyDictionary = WeakKeyDictionary()
+_clients_to_close: WeakSet = WeakSet()
 
 
 def _create_async_client(
@@ -48,13 +49,15 @@ def _create_async_client(
     # https://github.com/googleapis/gapic-generator-python/issues/1962
     if transport == "rest":
         transport = "grpc_asyncio"
-    return genaix.build_generative_async_service(
+    client = genaix.build_generative_async_service(
         credentials=None,
         api_key=api_key,
         client_info=get_client_info(f"ChatGoogleGenerativeAI:{model}"),
         client_options=None,
         transport=transport,
     )
+    _clients_to_close.add(client)
+    return client
 
 
 def _get_async_client(
@@ -88,3 +91,27 @@ def _get_async_client(
         )
 
     return _client_caches[loop][cache_key]
+
+
+# import atexit
+
+# import asyncio, atexit
+
+# _cleanup_loop = asyncio.new_event_loop()
+
+# async def _close_everything():
+#     await asyncio.gather(
+#         *(c.transport.close() for c in _clients_to_close),
+#         return_exceptions=True,
+#     )
+#     # let grpc.aio finish any pending callbacks
+#     await asyncio.sleep(0)
+
+# def _shutdown_all_clients():
+#     try:
+#         _cleanup_loop.run_until_complete(_close_everything())
+#         _cleanup_loop.run_until_complete(_cleanup_loop.shutdown_asyncgens())
+#     finally:
+#         _cleanup_loop.close()
+
+# atexit.register(_shutdown_all_clients)
diff --git a/libs/genai/langchain_google_genai/chat_models.py b/libs/genai/langchain_google_genai/chat_models.py
index 90f761741..8b480015c 100644
--- a/libs/genai/langchain_google_genai/chat_models.py
+++ b/libs/genai/langchain_google_genai/chat_models.py
@@ -1183,6 +1183,17 @@ def validate_environment(self) -> Self:
         atexit.register(self.client.transport.close)
         return self
 
+    # @atexit.register
+    # def close_async_client(self) -> None:
+    #     """Close the async client."""
+    #     loop = asyncio.get_event_loop()
+    #     loop.run_until_complete(self.await_close_async_client())
+
+    # async def await_close_async_client(self) -> None:
+    #     """Close the async client."""
+    #     if self.async_client_running:
+    #         await self.async_client_running.transport.close()
+
     @property
     def async_client(self) -> v1betaGenerativeServiceAsyncClient:
         google_api_key = None
@@ -1213,6 +1224,10 @@ def async_client(self) -> v1betaGenerativeServiceAsyncClient:
                 )
         return self.async_client_running
 
+    # async def __aexit__(self) -> None:
+    #     if self.async_client_running:
+    #         await self.async_client_running.transport.close()
+
     @property
     def _identifying_params(self) -> Dict[str, Any]:
         """Get the identifying parameters."""