gh-158010: Update Windows builds to use OpenSSL 3.5.9

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Change detection / Create context from changed files

Docs / Docs

Docs / Doctest

Docs / Check EPUB

Docs / Check for removed HTML IDs / Check for removed HTML IDs

Check if Autoconf files are up to date

Check if generated files are up to date

C API Docs / Check if all C APIs are documented

Windows / Build and test (x64, switch-case)

Windows (free-threading) / Build and test (x64, switch-case)

Windows / Build and test (Win32, switch-case)

Windows / Build and test (arm64, switch-case)

Windows (free-threading) / Build and test (arm64, switch-case)

Windows / Build and test (x64, tail-call)

Windows (free-threading) / Build and test (x64, tail-call)

macOS / build and test (macos-26)

macOS (free-threading) / build and test (macos-26)

macOS / build and test (macos-26-intel)

Ubuntu / build and test (ubuntu-26.04)

Ubuntu / build and test (ubuntu-26.04-arm)

Ubuntu (free-threading) / build and test (ubuntu-26.04)

Ubuntu (free-threading) / build and test (ubuntu-26.04-arm)

Ubuntu (bolt) / build and test (ubuntu-26.04)

Ubuntu (installed) / build, install and test

Ubuntu SSL tests (ubuntu-26.04, openssl, 1.1.1w)

Ubuntu SSL tests (ubuntu-26.04, openssl, 3.4.8)

Ubuntu SSL tests (ubuntu-26.04, openssl, 3.5.9)

Ubuntu SSL tests (ubuntu-26.04, openssl, 3.6.5)

Ubuntu SSL tests (ubuntu-26.04, openssl, 4.0.3)

Ubuntu SSL tests (ubuntu-26.04, aws-lc, 5.10.0)

Android (aarch64)

Android (x86_64)

iOS

Emscripten / build and test

WASI / build and test

Hypothesis tests on Ubuntu

Lazy imports enabled / Run Tests with lazy_imports=all

Address sanitizer (ubuntu-26.04)

Sanitizers / TSan

Sanitizers / TSan (free-threading)

Sanitizers / UBSan

Cross build Linux

CIFuzz${{ '' }}

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This PR is labelled type-feature. All features require approval from a core team member before merge. Found: type-feature, awaiting core review

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failed Sep 29, 2026 in 8s

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gh-158010: Update Windows builds to use OpenSSL 3.5.9

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