Bumps [urllib3](https://github.com/urllib3/urllib3) from 2.7.0 to 2.8.0. <details> <summary>Release notes</summary> <p><em>Sourced from <a href="https://github.com/urllib3/urllib3/releases">urllib3's releases</a>.</em></p> <blockquote> <h2>2.8.0</h2> <h2>🚀 urllib3 is fundraising for HTTP/2 support</h2> <p><a href="https://sethmlarson.dev/urllib3-is-fundraising-for-http2-support">urllib3 is raising ~$40,000 USD</a> to release HTTP/2 support and ensure long-term sustainable maintenance of the project. If your company or organization uses Python and would benefit from HTTP/2 support in Requests, pip, cloud SDKs, and thousands of other projects <a href="https://opencollective.com/urllib3">please consider contributing financially</a> to ensure HTTP/2 support is developed sustainably and maintained for the long-haul.</p> <p>Thank you for your support.</p> <h2>Security</h2> <p>Fixed the following security issues:</p> <ul> <li>The TLS configuration for HTTPS proxies could be ignored or overridden. (High severity, GHSA-8988-9cw3-xx77)</li> <li><code>HTTPResponse.stream()</code> and <code>read_chunked()</code> could buffer a chunk-size line of unbounded length in memory. (High severity, GHSA-vxq7-64xx-v4gw)</li> <li>Chunked Deflate streaming could enter an infinite loop. (Medium severity, GHSA-gh4c-6fx4-qh6g)</li> </ul> <blockquote> <p>[!IMPORTANT] urllib3 2.8.0 fixes HTTPS proxy TLS configuration being ignored or overridden by destination settings. Configurations relying on that behavior may require changes.</p> <p>Configure proxy CA certificates and client certificates in <code>proxy_ssl_context</code>, and proxy identity checks with <code>proxy_assert_hostname</code> or <code>proxy_assert_fingerprint</code>. Destination client certificates and identity overrides no longer apply to HTTPS forwarding proxy connections.</p> </blockquote> <blockquote> <p>[!NOTE] CVE IDs had not yet been assigned to these advisories at the time of release due to a backlog at GitHub's CNA.</p> </blockquote> <h2>Deprecations & Removals</h2> <ul> <li>Deprecated using an empty collection as the <code>Retry</code> option <code>allowed_methods</code> to retry any verb. (<a href="https://redirect.github.com/urllib3/urllib3/issues/5044">#5044</a>)</li> </ul> <h2>Features</h2> <ul> <li>Added <code>Url.auth_decoded</code> and <code>Url.auth_decoded_joined</code> convenience properties to the result of <code>parse_url()</code>. (<a href="https://redirect.github.com/urllib3/urllib3/issues/4945">#4945</a>)</li> <li>Added <code>basic_auth_encoding</code> and <code>proxy_basic_auth_encoding</code> parameters to <code>urllib3.util.make_headers()</code>. (<a href="https://redirect.github.com/urllib3/urllib3/issues/5092">#5092</a>)</li> </ul> <h2>Bugfixes</h2> <ul> <li> <p>Fixed response header handling to replace obsolete folded header lines (<code>obs-fold</code>) with spaces in accordance with RFC 9112, preventing raw CRLF sequences from appearing in header values such as <code>Set-Cookie</code>. (<a href="https://redirect.github.com/urllib3/urllib3/issues/1362">#1362</a>)</p> </li> <li> <p>Fixed usage of <code>proxy_ssl_context</code> with <code>ProxyManager</code> when <code>use_forwarding_for_https=True</code>. Passing <code>ssl_context</code> instead of <code>proxy_ssl_context</code> for HTTPS proxies in this configuration now emits a <code>FutureWarning</code> and will raise an error in v3.0. (<a href="https://redirect.github.com/urllib3/urllib3/issues/2577">#2577</a>)</p> </li> <li> <p>Changed behavior of the default <code>ConnectionPool.pool</code> initialization. <code>LifoQueue</code> is now resolved from the <code>queue</code> module after the <code>ConnectionPool</code> is instantiated instead of using the default cached <code>QueueCls</code> class property. This is done because sometimes the <code>queue.LifoQueue</code> is monkey-patched late in the program, such as by gevent. (<a href="https://redirect.github.com/urllib3/urllib3/issues/3289">#3289</a>)</p> </li> <li> <p>Raised <code>UnrewindableBodyError</code> instead of <code>ValueError</code> when retrying a request whose body had <code>tell()</code> but not <code>seek()</code>. (<a href="https://redirect.github.com/urllib3/urllib3/issues/3779">#3779</a>)</p> </li> <li> <p>Decoded percent-encoded SOCKS proxy credentials before authenticating with the proxy server. (<a href="https://redirect.github.com/urllib3/urllib3/issues/3785">#3785</a>)</p> </li> <li> <p>Fixed <code>HTTPResponse.drain_conn()</code> to discard unread response data in 64 KiB chunks (same as the default <code>amt</code> when doing <code>HTTPResponse.stream(...)</code>). (<a href="https://redirect.github.com/urllib3/urllib3/issues/5019">#5019</a>)</p> </li> <li> <p>Fixed <code>is_ipaddress()</code> to detect non-standard IPv4 forms accepted by <code>socket.connect</code>, such as hex (<code>0x7f000001</code>), octal (<code>0177.0.0.1</code>), and decimal integers (<code>2130706433</code>), ensuring SSL certificate verification uses the correct mode for these addresses. (<a href="https://redirect.github.com/urllib3/urllib3/issues/5029">#5029</a>)</p> </li> <li> <p>Fixed <code>HTTPConnectionPool.urlopen</code> raising a misleading <code>FullPoolError</code> instead of <code>ValueError</code> when called with an invalid <code>timeout</code> argument on a pool created with <code>block=True</code>. (<a href="https://redirect.github.com/urllib3/urllib3/issues/5059">#5059</a>)</p> </li> <li> <p>Fixed port-zero handling to preserve explicit <code>:0</code> values instead of substituting the default ports 80 or 443 in URL parsing, pool selection, proxy configuration, <code>connection_from_url()</code>, and HTTP/2 request authority. (<a href="https://redirect.github.com/urllib3/urllib3/issues/5071">#5071</a>, <a href="https://redirect.github.com/urllib3/urllib3/issues/5101">#5101</a>)</p> </li> <li> <p>Fixed a bug where <code>PoolManager</code> passed the <code>assert_hostname</code> and <code>assert_fingerprint</code> parameters to HTTP connection pools. (<a href="https://redirect.github.com/urllib3/urllib3/issues/5077">#5077</a>)</p> </li> <li> <p>Fixed <code>HTTPConnectionPool.urlopen()</code> and HTTP proxy forwarding to strip URL fragments from absolute request targets before sending requests. (<a href="https://redirect.github.com/urllib3/urllib3/issues/5079">#5079</a>)</p> </li> <li> <p>Added safeguards to the proxy tunneling code to prevent potential security issues when handling invalid characters in the proxy host and HTTP headers. This change affects users of Python 3.10, Python 3.11, and Python 3.12 when the standard library does not contain the fix; those on newer Python versions should upgrade to 3.13.14+ or 3.14.5+ to get the same security fixes. (<a href="https://redirect.github.com/urllib3/urllib3/issues/5091">#5091</a>)</p> </li> <li> <p>Fixed <code>HTTPSConnection.connect()</code> overriding <code>ProxyConfig.ssl_context</code>'s certificate policy and proxy identity checks with the target connection's TLS settings when forwarding through an HTTPS proxy.</p> <p><code>HTTPSConnection</code> no longer applies target SNI, assertions, or client credentials to forwarding proxy handshakes and continues to use its <code>ssl_context</code> as a fallback when an HTTPS proxy forwards an HTTP target. (<a href="https://redirect.github.com/urllib3/urllib3/issues/5093">#5093</a>)</p> </li> <li> <p>Fixed URL parsing to more strictly enforce RFC 3986 host syntax, rejecting invalid host input such as raw spaces and control characters, malformed percent-encodings, and percent-encoded control characters in HTTP(S) hosts and IPv6 zone identifiers, including proxy CONNECT tunnel targets. Host normalization now also follows RFC 3986 normalization rules for percent-encoded octets by decoding percent-encoded unreserved characters and uppercasing the hexadecimal digits of retained percent-encoded octets. (<a href="https://redirect.github.com/urllib3/urllib3/issues/5095">#5095</a>)</p> </li> </ul> <!-- raw HTML omitted --> </blockquote> <p>... (truncated)</p> </details> <details> <summary>Changelog</summary> <p><em>Sourced from <a href="https://github.com/urllib3/urllib3/blob/main/CHANGES.rst">urllib3's changelog</a>.</em></p> <blockquote> <h1>2.8.0 (2026-09-15)</h1> <h2>Security</h2> <p>Fixed the following security issues:</p> <ul> <li>The TLS configuration for HTTPS proxies could be ignored or overridden. (High severity, <code>GHSA-8988-9cw3-xx77 <https://github.com/urllib3/urllib3/security/advisories/GHSA-8988-9cw3-xx77></code>__)</li> <li><code>HTTPResponse.stream()</code> and <code>read_chunked()</code> could buffer a chunk-size line of unbounded length in memory. (High severity, <code>GHSA-vxq7-64xx-v4gw <https://github.com/urllib3/urllib3/security/advisories/GHSA-vxq7-64xx-v4gw></code>__)</li> <li>Chunked Deflate streaming could enter an infinite loop. (Medium severity, <code>GHSA-gh4c-6fx4-qh6g <https://github.com/urllib3/urllib3/security/advisories/GHSA-gh4c-6fx4-qh6g></code>__)</li> </ul> <p>.. caution::</p> <pre><code>urllib3 2.8.0 fixes HTTPS proxy TLS configuration being ignored or overridden by destination settings. Configurations relying on that behavior may require changes. <p>Configure proxy CA certificates and client certificates in <code>proxy_ssl_context</code>, and proxy identity checks with <code>proxy_assert_hostname</code> or <code>proxy_assert_fingerprint</code>. Destination client certificates and identity overrides no longer apply to HTTPS forwarding proxy connections. </code></pre></p> <h2>Deprecations & Removals</h2> <ul> <li>Deprecated using an empty collection as the <code>Retry</code> option <code>allowed_methods</code> to retry any verb. (<code>[#5044](https://github.com/urllib3/urllib3/issues/5044) <https://github.com/urllib3/urllib3/issues/5044></code>__)</li> </ul> <h2>Features</h2> <ul> <li>Added <code>Url.auth_decoded</code> and <code>Url.auth_decoded_joined</code> convenience properties to the result of <code>parse_url()</code>. (<code>[#4945](https://github.com/urllib3/urllib3/issues/4945) <https://github.com/urllib3/urllib3/issues/4945></code>__)</li> <li>Added <code>basic_auth_encoding</code> and <code>proxy_basic_auth_encoding</code> parameters to <code>urllib3.util.make_headers()</code>. (<code>[#5092](https://github.com/urllib3/urllib3/issues/5092) <https://github.com/urllib3/urllib3/issues/5092></code>__)</li> </ul> <h2>Bugfixes</h2> <!-- raw HTML omitted --> </blockquote> <p>... (truncated)</p> </details> <details> <summary>Commits</summary> <ul> <li><a href="https://github.com/urllib3/urllib3/commit/b1d30ab61fe0db8f11092805e8c5ac43e091064a"><code>b1d30ab</code></a> Release 2.8.0</li> <li><a href="https://github.com/urllib3/urllib3/commit/9016d7e8afc68185496ef07f3c3a4a743d04922e"><code>9016d7e</code></a> Skip <code>test_read_chunked_with_trailing_data_does_not_hang</code> for brotlicffi (<a href="https://redirect.github.com/urllib3/urllib3/issues/5258">#5258</a>)</li> <li><a href="https://github.com/urllib3/urllib3/commit/9101f581a8b3659af23b6ff335ae77200ca33533"><code>9101f58</code></a> Fix <code>nox -s docs</code> warning (<a href="https://redirect.github.com/urllib3/urllib3/issues/5256">#5256</a>)</li> <li><a href="https://github.com/urllib3/urllib3/commit/cd770b059b543be29298ea5c52afb0b1b090f5ed"><code>cd770b0</code></a> Merge commit from fork</li> <li><a href="https://github.com/urllib3/urllib3/commit/ea2ad7b21a80da3632f80016526a18864586077f"><code>ea2ad7b</code></a> Merge commit from fork</li> <li><a href="https://github.com/urllib3/urllib3/commit/0716e31534345dc1599ea95d903c79f276239bd8"><code>0716e31</code></a> Fix loading unencrypted client keys with a password in pyOpenSSL (<a href="https://redirect.github.com/urllib3/urllib3/issues/5255">#5255</a>)</li> <li><a href="https://github.com/urllib3/urllib3/commit/43c68c8b43a9dcb44ed2cf4ec91384ca0d46b37d"><code>43c68c8</code></a> Test pickling of <code>InvalidChunkLength</code> (<a href="https://redirect.github.com/urllib3/urllib3/issues/5247">#5247</a>)</li> <li><a href="https://github.com/urllib3/urllib3/commit/308b279b3fb28e7bee952e152ec5baeb5bfd0817"><code>308b279</code></a> Share security policy between GitHub and Read the Docs (<a href="https://redirect.github.com/urllib3/urllib3/issues/5253">#5253</a>)</li> <li><a href="https://github.com/urllib3/urllib3/commit/53fa0731b27d4b71ab0755ea5b896422d005d706"><code>53fa073</code></a> Add policy on duplicate pull requests (<a href="https://redirect.github.com/urllib3/urllib3/issues/5252">#5252</a>)</li> <li><a href="https://github.com/urllib3/urllib3/commit/5f2a6a843d0100d1351c3f94d58581ca98d17267"><code>5f2a6a8</code></a> Assert on the ALPN extension in test_tunnel_sets_http_11_alpn (<a href="https://redirect.github.com/urllib3/urllib3/issues/5232">#5232</a>)</li> <li>Additional commits viewable in <a href="https://github.com/urllib3/urllib3/compare/2.7.0...2.8.0">compare view</a></li> </ul> </details> <br /> Signed-off-by: dependabot[bot] <support@github.com> Co-authored-by: dependabot[bot] <49699333+dependabot[bot]@users.noreply.github.com>
The agent engineering platform.
LangChain is a framework for building agents and LLM-powered applications. It helps you chain together interoperable components and third-party integrations to simplify AI application development — all while future-proofing decisions as the underlying technology evolves.
Tip
Just getting started? Check out Deep Agents — a higher-level package built on LangChain for agents that have built-in capabilities for common usage patterns such as planning, subagents, file system usage, and more.
Quickstart
uv add langchain
from langchain.chat_models import init_chat_model
model = init_chat_model("openai:gpt-5.5")
result = model.invoke("Hello, world!")
If you're looking for more advanced customization or agent orchestration, check out LangGraph, our framework for building controllable agent workflows.
For an equivalent JS/TS library, check out LangChain.js.
Tip
For developing, debugging, and deploying AI agents and LLM applications, see LangSmith.
LangChain ecosystem
While the LangChain framework can be used standalone, it also integrates seamlessly with any LangChain product, giving developers a full suite of tools when building LLM applications.
- Deep Agents — Build agents that can plan, use subagents, and leverage file systems for complex tasks
- LangGraph — Build agents that can reliably handle complex tasks with our low-level agent orchestration framework
- Integrations — Chat & embedding models, tools & toolkits, and more
- LangSmith — Agent evals, observability, and debugging for LLM apps
- LangSmith Deployment — Deploy and scale agents with a purpose-built platform for long-running, stateful workflows
Why use LangChain?
LangChain helps developers build applications powered by LLMs through a standard interface for models, embeddings, vector stores, and more.
- Real-time data augmentation — Easily connect LLMs to diverse data sources and external/internal systems, drawing from LangChain's vast library of integrations with model providers, tools, vector stores, retrievers, and more
- Model interoperability — Swap models in and out as your engineering team experiments to find the best choice for your application's needs. As the industry frontier evolves, adapt quickly — LangChain's abstractions keep you moving without losing momentum
- Rapid prototyping — Quickly build and iterate on LLM applications with LangChain's modular, component-based architecture. Test different approaches and workflows without rebuilding from scratch, accelerating your development cycle
- Production-ready features — Deploy reliable applications with built-in support for monitoring, evaluation, and debugging through integrations like LangSmith. Scale with confidence using battle-tested patterns and best practices
- Vibrant community and ecosystem — Leverage a rich ecosystem of integrations, templates, and community-contributed components. Benefit from continuous improvements and stay up-to-date with the latest AI developments through an active open-source community
- Flexible abstraction layers — Work at the level of abstraction that suits your needs — from high-level chains for quick starts to low-level components for fine-grained control. LangChain grows with your application's complexity
Resources
- Documentation — conceptual overviews and guides
- LangChain ecosystem overview — how LangChain, LangGraph, and Deep Agents fit together
- API reference — complete reference for all public classes, functions, and types
- Discussions — community forum for technical questions, ideas, and feedback
- LangChain Academy — comprehensive, free courses on LangChain libraries and products, made by the LangChain team
- Contributing Guide — how to contribute and find good first issues
- Code of Conduct — community guidelines and standards