[macOS] OpenSSL 1.1 will be removed and OpenSSL 3 will be the default for all macOS images once [date not determined]

[sarathrajsrinivasan]

Breaking changes

OpenSSL 1.1 will be removed from all macOS images and the default version will be switched to OpenSSL 3.

Target date

⚠️ We will notify you of planned changes when exact dates are set. ⚠️

The motivation for the changes

OpenSSL 1.1 has reached its end-of-life (EOL) and is no longer supported. Due to its deprecation, Homebrew has removed it from its available packages.

Possible impact

If your library/project is not compatible with OpenSSL 3 and you build them based on default OpenSSL version - your workflow will be broken.

Platforms affected

• Azure DevOps
• GitHub Actions

Runner images affected

• Ubuntu 20.04
• Ubuntu 22.04
• Ubuntu 24.04
• macOS 12
• macOS 13
• macOS 13 Arm64
• macOS 14
• macOS 14 Arm64
• macOS 15
• macOS 15 Arm64
• Windows Server 2019
• Windows Server 2022

Mitigation ways

Use the below step in your workflow to download and install OpenSSL 1.1 manually

    - name : Install  OpenSSL 1.1 manually
      run : |
        wget https://www.openssl.org/source/openssl-1.1.1w.tar.gz
        tar -xvf openssl-1.1.1w.tar.gz
        cd openssl-1.1.1w
        ./config --prefix=/usr/local/openssl
        make
        sudo make install
        export PATH=/usr/local/openssl/bin:$PATH

[eregon]

This means currently some runs on macos-14 have openssl@1.1 and some don't:
https://github.com/eregon/setup-ruby/actions/runs/11724213556/job/32657603152

This is quite problematic because if something is built on macos-14 on a run with openssl@1.1 (and the software links to that) it can fail when that's later used in another run as openssl@1.1 /opt/homebrew/opt/openssl@1.1/lib/libssl.1.1.dylib is gone.

Basically, anything that ever linked to openssl@1.1 on macos-* will be broken by this change (until it's recompiled against openssl@3).

[jorupp]

Is there a way to configure our build so we only run on the OpenSSL@3-equipped images? We can't add the -legacy flag we need for OpenSSL@3 (called within InstallAppleCertificate@2's pre-job) because it breaks when the build runs on an openssl@1.1.1-equipped image, and we can't manually install openssl@1.1.1 via a script because the call to openssl is in InstallAppleCertificate@2's pre-job.

[jorupp]

We worked around it with InstallAppleCertificate@2 by putting two copies of the task in our pipeline - one with opensslPkcsArgs: -legacy and one without, and with continueWithError: true on both so the one that fails won't fail our build.

[mikeharder]

Could this change be breaking actions/setup-python on Mac?

#10812 (comment)

[altendky]

In this test run https://github.com/Chia-Network/chia-blockchain/actions/runs/11745259139?pr=18844 with 30x each of macOS ARM/Intel and Python version 3.9/3.10/3.11/3.12, only 3.10 on Intel failed. The passing jobs were run on either 20241008.186 or 20241023.237. The failing jobs were on 20241107.313.

[mikeharder]

In this test run https://github.com/Chia-Network/chia-blockchain/actions/runs/11745259139?pr=18844 with 30x each of macOS ARM/Intel and Python version 3.9/3.10/3.11/3.12, only 3.10 on Intel failed. The passing jobs were run on either 20241008.186 or 20241023.237. The failing jobs were on 20241107.313.

I think we might be seeing a combination of both #10817 and #10812. In your test run, Python 3.10 was found in the cache on macOS ARM64, so it passes. But if you land on an agent without Python 3.10 in the cache, it will try to download and install, but fails with the SSL error.