Cask update broke Parallels uninstallation

[v-SergeiRadich]

Verification

• I understand that if I ignore these instructions, my issue may be closed without review.
• I have retried my command with --force.
• I ran brew update-reset && brew update and retried my command.
• I ran brew doctor, fixed as many issues as possible and retried my command.
• I have checked the instructions for reporting bugs.
• I made doubly sure this is not a checksum does not match / SHA256 mismatch error (do not open an issue before trying to open a PR to fix first).
• I did not use AI/LLM to create this issue, or I disclosed the tool and model used; I will answer maintainer questions myself without AI/LLM.

Description of issue

After update of Parallels cask brew uninstall --cask parallels command fails to execute. This led to broken builds for GitHub Actions team.

We were able to mitigate issue by pinning previous version of cask.

Workflow with repro: https://github.com/v-SergeiRadich/Testing_Repo_Public/actions/runs/31163198634

Usage of --force or --zap had no effect.

Command that failed

brew uninstall --cask parallels

Output of command with --verbose --debug

==> Uninstalling artifact of class Cask::Artifact::PreflightSteps
==> Uninstalling artifact of class Cask::Artifact::UninstallPreflightSteps
/usr/bin/sudo -E -- touch /Applications/Parallels\ Desktop.app/.homebrew-write-test
/usr/bin/sudo -E -- rm /Applications/Parallels\ Desktop.app/.homebrew-write-test
==> Changing ownership of paths required by parallels with `sudo` (which may request your password)...
/usr/bin/sudo -E -- chown -R -- runner:staff /Applications/Parallels\ Desktop.app
==> Uninstalling artifact of class Cask::Artifact::Uninstall
==> Signalling 'TERM' to application ID 'com.parallels.desktop.console'
/usr/bin/env /bin/launchctl list
==> Running uninstall script /usr/bin/pkill
/usr/bin/env /usr/bin/pkill -TERM prl_client_app
Error: Failure while executing; `/usr/bin/env /usr/bin/pkill -TERM prl_client_app` exited with 1.

Output of brew doctor and brew config

brew doctor:
Please note that these warnings are just used to help the Homebrew maintainers
with debugging if you file an issue. If everything you use Homebrew for is
working fine: please don't worry or file an issue; just ignore this. Thanks!

Warning: Some installed kegs have no formulae!
This means they were either deleted or installed manually.


You should find replacements for the following formulae:
  openssl@1.1

Warning: Some installed formulae are deprecated or disabled.
You should find replacements for the following formulae:
    openssl@1.1

Warning: You have an unnecessary local Cask tap.
This can cause problems installing up-to-date casks.

Please remove it by running:
 brew untap homebrew/cask

Warning: You have an unnecessary local Core tap!
This can cause problems installing up-to-date formulae.

Please remove it by running:
 brew untap homebrew/core

Warning: You have uncommitted modifications to Homebrew/homebrew-core.
Uncommitted files:
  ?? Formula/o/openssl@1.1.rb

If this is a surprise to you, then you should stash these modifications.
Stashing returns Homebrew to a pristine state but can be undone
should you later need to do so for some reason.

  git -C "/opt/homebrew/Library/Taps/homebrew/homebrew-core" stash -u && git -C "/opt/homebrew/Library/Taps/homebrew/homebrew-core" clean -d -f

Warning: The following taps are not trusted:
  aws/tap

Homebrew is currently ignoring formulae, casks and commands from these taps because tap trust is required.

Untap them with:
  brew untap aws/tap
Trust specific formulae, casks and commands with:
  brew trust --formula <user>/<tap>/<formula>
  brew trust --cask <user>/<tap>/<cask>
  brew trust --command <user>/<tap>/<command>
Whole-tap trust is broader and includes all current and future formulae,
casks and commands from the listed taps. Trust whole taps with:
  brew trust aws/tap
To disable trust checks:
  export HOMEBREW_NO_REQUIRE_TAP_TRUST=1
This is not recommended and will be removed in a later release.
For more information, see:
  https://docs.brew.sh/Tap-Trust

brew config:
HOMEBREW_VERSION: 6.0.15
ORIGIN: https://github.com/Homebrew/brew
HEAD: 7b0f22a4ab77567edef114c8dfc423fb96e2fbaa
Last commit: 4 days ago
Branch: stable
Core tap HEAD: 497c4ab25d202baf7024d7f2a30eb17e3056c694
Core tap last commit: 7 minutes ago
Core tap JSON: 07 Aug 08:48 UTC
Core cask tap HEAD: c496d2466ca51b9d6feb8fb4a647f8f62a4fcd66
Core cask tap last commit: 10 minutes ago
Core cask tap JSON: 07 Aug 08:48 UTC
HOMEBREW_PREFIX: /opt/homebrew
HOMEBREW_CASK_OPTS: ["--no-quarantine"]
HOMEBREW_NO_AUTO_UPDATE: set
HOMEBREW_NO_INSTALL_CLEANUP: set
Homebrew Ruby: 4.0.6 => /opt/homebrew/Library/Homebrew/vendor/portable-ruby/4.0.6/bin/ruby
CPU: 3-core 64-bit dunno
Clang: 15.0.0 build 1500
Git: 2.54.0 => /opt/homebrew/bin/git
Curl: 8.7.1 => /usr/bin/curl
macOS: 14.8.7-arm64
CLT: 16.2.0.0.1.1733547573
Xcode: 15.4 => /Applications/Xcode_15.4.app/Contents/Developer
Rosetta 2: false

Output of brew tap

aws/tap
azure/bicep
hashicorp/tap
homebrew/cask
homebrew/core

[v-SergeiRadich]

Side note - Homebrew's latest security policy changes does not allow to use any of ways listed in your USAGE.MD to pin a cask, we had to work around it with some pain.

[SSakutaro]

I was planning to submit a fix, but something unexpected came up.
If no PR addressing this issue has been opened by tomorrow, I’ll work on one.

[SSakutaro]

@v-SergeiRadich

This has been fixed in Homebrew/brew#23478.

The generated Cask API data was dropping the explicit must_succeed: false value from the Parallels uninstall script. As a result, the script fell back to must_succeed: true, and pkill exiting with status 1 interrupted the uninstall when prl_client_app was not running.

Please update Homebrew and try the uninstall again:

brew update
brew remove --cask parallels

After clearing my local Homebrew cache and updating Homebrew, I confirmed that the refreshed internal API contains must_succeed: false and that Parallels can be uninstalled successfully.

As an aside, if you also want to remove Parallels-related caches, preferences, and other associated files, you can uninstall it with --zap:

brew uninstall --cask --zap parallels

Please note that --zap removes additional user data and configuration files, so review the Cask's zap stanza before running it.