`brew update && brew upgrade -q` fails

[limentas]

Description

Today I experience a lot of errors on macos runners. It seems to me that this is a regression in the latest image.
The problem is that brew update && brew upgrade -q fails.

Platforms affected

• Azure DevOps
• GitHub Actions - Standard Runners
• GitHub Actions - Larger Runners

Runner images affected

• Ubuntu 22.04
• Ubuntu 24.04
• Ubuntu Slim
• macOS 14
• macOS 14 Arm64
• macOS 15
• macOS 15 Arm64
• macOS 26
• macOS 26 Arm64
• Windows Server 2022
• Windows Server 2025
• Windows Server 2025 with Visual Studio 2026

Image version and build link

Image: macos-15-arm64
Version: 20260325.0234.1

Is it regression?

Yes. It worked in 20260303.0188.2

Expected behavior

brew update && brew upgrade -q finishes succsefully

Actual behavior

brew update && brew upgrade -q finishes with error:

2026-03-27T08:17:05.3751510Z ##[error]The `brew link` step did not complete successfully
2026-03-27T08:17:05.3764480Z The formula built, but is not symlinked into /opt/homebrew
2026-03-27T08:17:05.3796180Z Could not symlink lib/ruby/gems/3.3.0/doc/rubygems-4.0.9/ri/CoreExtensions/TCPSocketExt/Initializer/cdesc-Initializer.ri
2026-03-27T08:17:05.3897100Z Target /opt/homebrew/lib/ruby/gems/3.3.0/doc/rubygems-4.0.9/ri/CoreExtensions/TCPSocketExt/Initializer/cdesc-Initializer.ri
2026-03-27T08:17:05.3997970Z already exists. You may want to remove it:
2026-03-27T08:17:05.4099010Z   rm '/opt/homebrew/lib/ruby/gems/3.3.0/doc/rubygems-4.0.9/ri/CoreExtensions/TCPSocketExt/Initializer/cdesc-Initializer.ri'
2026-03-27T08:17:05.4200050Z 
2026-03-27T08:17:05.4301000Z To force the link and overwrite all conflicting files:
2026-03-27T08:17:05.4402090Z   brew link --overwrite ruby@3.3
2026-03-27T08:17:05.4502750Z 
2026-03-27T08:17:05.4571000Z To list all files that would be deleted:
2026-03-27T08:17:05.4572340Z   brew link --overwrite ruby@3.3 --dry-run
2026-03-27T08:17:05.4572770Z 
2026-03-27T08:17:05.4572990Z Possible conflicting files are:
...
2026-03-27T08:17:18.7232340Z ##[error]Process completed with exit code 1.

Repro steps

Part of workflow file that fails:

      - name: Install non-cacheable dependencies
        run: |
          echo -- Installing nasm to build FFmpeg
          brew update && brew upgrade -q
          brew install nasm

[v-SergeiRadich]

Hi!

Thank you for reporting - we will check it.

[v-sergei-pyshnoi]

Hi @limentas 👋 !
Looks problem in new ruby@3.3 formula version. During updating form 3.10 -> 3.11 for some reason its cannot create link properly. In new image update problem resolved since it already have 3.11 preinstalled. Before new image version will be available widely as workaround you can use brew upgrade --overwrite in you workflow to overwrite links for all packages or just for ruby with brew upgrade ruby@3.3 --overwrite

[limentas]

@v-sergei-pyshnoi
Thanks for the fix