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ci: upgrade OpenSSL on macOS runners before building - #55
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The cryptography wheel bundled by PyInstaller references _SSL_get0_group_name (added in OpenSSL 3.2), but the macos-15-intel runner has an older libssl.3.dylib that doesn't export this symbol, causing the smoke test to crash. Upgrading openssl@3 before the build ensures PyInstaller bundles a compatible dylib. Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
alexrashed
marked this pull request as draft
June 22, 2026 06:47
cryptography 49.0.0 has no pre-built wheel for macOS x86_64 and builds from source. The Rust openssl-sys crate picks up Python's OpenSSL via PKG_CONFIG_PATH (set by setup-python), which differs from the Homebrew libssl.3.dylib that PyInstaller later bundles — so _SSL_get0_group_name is present at compile time but missing at runtime. Setting OPENSSL_STATIC=1 and OPENSSL_DIR forces static linking against Homebrew's OpenSSL, embedding all required symbols into _rust.abi3.so and eliminating the libssl.3.dylib runtime dependency entirely. The timeout is bumped to 10 min to allow for the longer static link step. Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
cryptography 49.0.0 has no pre-built macOS x86_64 wheel and builds from Rust source. setup-python sets PKG_CONFIG_PATH to Python's own OpenSSL, which openssl-sys picks up for headers during compilation — but PyInstaller later bundles Homebrew's libssl.3.dylib from /usr/local/opt/openssl@3. These two OpenSSL builds differ, so _SSL_get0_group_name is present at compile time but missing at runtime. Setting OPENSSL_DIR=/usr/local/opt/openssl@3 forces openssl-sys to use Homebrew's headers and link against Homebrew's dylib, ensuring the compile-time and runtime libraries match. Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
cryptography 49.0.0 dropped macOS x86_64 wheel publishing and switched to AWS-LC as its Rust backend. Building from source on macos-15-intel produces a _rust.abi3.so that references _SSL_get0_group_name (an AWS-LC extension), but PyInstaller bundles standard OpenSSL's libssl.3.dylib which lacks this symbol, causing a crash at runtime. Pinning to <49 ensures pip selects 48.0.1, which ships a universal2 wheel with a properly delocated OpenSSL for both arm64 and x86_64. Reverts the now-unnecessary OPENSSL_DIR workflow workaround. Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
Move the pin out of requirements.txt (which affects all platforms) and into a runner-specific PIP_CONSTRAINT set via GITHUB_ENV. All other runners continue to get the latest cryptography. Co-Authored-By: Claude Sonnet 4.6 <noreply@anthropic.com>
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Summary
This issue was discovered in this run triggerd for #54:
macos-15-intelsmoke test was crashing because thecryptographywheel's Rust extension (_rust.abi3.so) references_SSL_get0_group_name(added in OpenSSL 3.2), but PyInstaller was bundling an olderlibssl.3.dylibfrom the runner that doesn't export that symbol.cryptographyversion to<49for MacOS x86_64.This is just a dirty fix to keep the CLI alive. We should officially deprecate the CLI for x86_64 MacOS as well.
Test plan
build (macos-15-intel, darwin, amd64)job passes the Non-Docker Smoke tests stepmacos-14(arm64) and other runners