Error upgrading to GIMP 3.0.0 from latest 2.x: Can't find /Applications/GIMP.app

[brianrobt]

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).

Description of issue

When upgrading GIMP from the latest 2.x release to 3.0.0, I received the following error (below output is from running brew upgrade):

==> Upgrading 1 outdated package:
gimp 2.10.38,1 -> 3.0.0,1
==> Upgrading gimp
==> Downloading https://raw.githubusercontent.com/Homebrew/homebrew-cask/4477d5b58a4fc668d9010aac20771622904efa8d/Casks/g/gimp.rb
############################################################################################################################################################################################################################################### 100.0%
==> Downloading https://download.gimp.org/gimp/v3.0/macos/gimp-3.0.0-arm64-1.dmg
Already downloaded: /Users/brian/Library/Caches/Homebrew/downloads/60211ce3bd25a8458e5abd7df6e7f2c7c88c6ebdf9829ffd04a6819104b28276--gimp-3.0.0-arm64-1.dmg
==> Purging files for version 3.0.0,1 of Cask gimp
Error: gimp: It seems the App source '/Applications/GIMP.app' is not there.

So, I tried uninstalling GIMP with brew uninstall --cask gimp --force. The command ran successfully, but when searching for GIMP with brew search gimp, the output showed that the GIMP cask was still installed.

I proceeded with force installing GIMP with brew install --cask gimp --force, and got a slightly different error:

> brew install --cask gimp --force
==> Upgrading 1 outdated package:
gimp 2.10.38,1 -> 3.0.0,1
==> Upgrading gimp
==> Downloading https://raw.githubusercontent.com/Homebrew/homebrew-cask/300a9b6376390c492e58f91ffc3e58de3c2f099d/Casks/g/gimp.rb
Already downloaded: /Users/brian/Library/Caches/Homebrew/downloads/fd126f227c5d39695a8c67c6d999eb841e328bbc6146e15c90c91108cf4fd12f--gimp.rb
==> Downloading https://download.gimp.org/gimp/v3.0/macos/gimp-3.0.0-arm64-1.dmg
Already downloaded: /Users/brian/Library/Caches/Homebrew/downloads/60211ce3bd25a8458e5abd7df6e7f2c7c88c6ebdf9829ffd04a6819104b28276--gimp-3.0.0-arm64-1.dmg
==> Purging files for version 3.0.0,1 of Cask gimp
Error: gimp: No such file or directory @ rb_file_s_rename - (/opt/homebrew/Caskroom/gimp/2.10.38,1, /opt/homebrew/Caskroom/gimp/2.10.38,1.upgrading)

Intervening manually solves the issue as seen below:

> find /opt/homebrew/Caskroom -name gimp
/opt/homebrew/Caskroom/gimp
/opt/homebrew/Caskroom/gimp/2.10.38,1.upgrading/GIMP.app/Contents/MacOS/gimp.dSYM/Contents/Resources/DWARF/gimp
/opt/homebrew/Caskroom/gimp/2.10.38,1.upgrading/GIMP.app/Contents/MacOS/gimp
/opt/homebrew/Caskroom/gimp/2.10.38,1.upgrading/GIMP.app/Contents/Resources/etc/gimp
/opt/homebrew/Caskroom/gimp/2.10.38,1.upgrading/GIMP.app/Contents/Resources/lib/gimp
/opt/homebrew/Caskroom/gimp/2.10.38,1.upgrading/GIMP.app/Contents/Resources/share/gimp

~/workspace/SSM/iht-azure/terraform-azure-vnet on main                                                                                                                                                             py base node system at 08:36:29 AM
> rm -rf /opt/homebrew/Caskroom/gimp

~/workspace/SSM/iht-azure/terraform-azure-vnet on main                                                                                                                                                             py base node system at 08:36:44 AM
> brew search gimp
==> Formulae
gmp ✔

==> Casks
gimp                                                                                                                        gimp@dev

~/workspace/SSM/iht-azure/terraform-azure-vnet on main                                                                                                                                                             py base node system at 08:36:50 AM
> brew install --cask gimp
==> Downloading https://formulae.brew.sh/api/cask.jws.json
==> Downloading https://raw.githubusercontent.com/Homebrew/homebrew-cask/300a9b6376390c492e58f91ffc3e58de3c2f099d/Casks/g/gimp.rb
Already downloaded: /Users/brian/Library/Caches/Homebrew/downloads/fd126f227c5d39695a8c67c6d999eb841e328bbc6146e15c90c91108cf4fd12f--gimp.rb
==> Downloading https://download.gimp.org/gimp/v3.0/macos/gimp-3.0.0-arm64-1.dmg
Already downloaded: /Users/brian/Library/Caches/Homebrew/downloads/60211ce3bd25a8458e5abd7df6e7f2c7c88c6ebdf9829ffd04a6819104b28276--gimp-3.0.0-arm64-1.dmg
==> Installing Cask gimp
==> Moving App 'GIMP.app' to '/Applications/GIMP.app'
==> Linking Binary 'gimp.wrapper.sh' to '/opt/homebrew/bin/gimp'
🍺  gimp was successfully installed!

However, I would've expected Homebrew to uninstall everything so that I could perform a clean install. The uninstall removed GIMP from /Applications, but didn't cleanup all the /opt/homebrew/Caskroom/gimp files. Also, after manual intervention, you can see the Homebrew no longer detects GIMP as installed after running brew search gimp.

Command that failed

brew install --cask gimp --force

Output of command with --verbose --debug

==> Downloading https://formulae.brew.sh/api/cask.jws.json
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --user-agent Homebrew/4.4.26\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.3.2\)\ curl/8.7.1 --header Accept-Language:\ en --fail --remote-time --output /Users/brian/Library/Caches/Homebrew/api/cask.jws.json --location --time-cond /Users/brian/Library/Caches/Homebrew/api/cask.jws.json --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.4.26\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.3.2\)\ curl/8.7.1 --header Accept-Language:\ en --fail --compressed --speed-limit 100 --speed-time 5 https://formulae.brew.sh/api/cask.jws.json
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading gimp
==> Upgrading 1 outdated package:
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromPathLoader): loading /opt/homebrew/Caskroom/gimp/.metadata/2.10.38,1.upgrading/20250228202809.794/Casks/gimp.rb
gimp 2.10.38,1 -> 3.0.0,1
==> Started upgrade process for Cask gimp
==> Upgrading gimp
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading gimp@dev
==> Printing caveats
==> Cask::Installer#fetch
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.4.26\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.3.2\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 -V
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.4.26\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.3.2\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 --fail --location --silent --head https://raw.githubusercontent.com/Homebrew/homebrew-cask/300a9b6376390c492e58f91ffc3e58de3c2f099d/Casks/g/gimp.rb
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.4.26\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.3.2\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 --fail --location --silent --head --request GET --http1.1 https://raw.githubusercontent.com/Homebrew/homebrew-cask/300a9b6376390c492e58f91ffc3e58de3c2f099d/Casks/g/gimp.rb
==> Downloading https://raw.githubusercontent.com/Homebrew/homebrew-cask/300a9b6376390c492e58f91ffc3e58de3c2f099d/Casks/g/gimp.rb
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.4.26\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.3.2\)\ curl/8.7.1 --header Accept-Language:\ en --fail --connect-timeout 15 --retry 3 --remote-time --output /Users/brian/Library/Caches/Homebrew/downloads/fd126f227c5d39695a8c67c6d999eb841e328bbc6146e15c90c91108cf4fd12f--gimp.rb.incomplete --location https://raw.githubusercontent.com/Homebrew/homebrew-cask/300a9b6376390c492e58f91ffc3e58de3c2f099d/Casks/g/gimp.rb
  % Total    % Received % Xferd  Average Speed   Time    Time     Time  Current
                                 Dload  Upload   Total   Spent    Left  Speed
100  1802  100  1802    0     0  28381      0 --:--:-- --:--:-- --:--:-- 28603
==> Verifying checksum for 'fd126f227c5d39695a8c67c6d999eb841e328bbc6146e15c90c91108cf4fd12f--gimp.rb'
==> Downloading https://download.gimp.org/gimp/v3.0/macos/gimp-3.0.0-arm64-1.dmg
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.4.26\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.3.2\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 -V
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.4.26\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.3.2\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 --fail --location --silent --head https://download.gimp.org/gimp/v3.0/macos/gimp-3.0.0-arm64-1.dmg
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.4.26\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.3.2\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 --fail --location --silent --head --request GET --http1.1 https://download.gimp.org/gimp/v3.0/macos/gimp-3.0.0-arm64-1.dmg
Already downloaded: /Users/brian/Library/Caches/Homebrew/downloads/60211ce3bd25a8458e5abd7df6e7f2c7c88c6ebdf9829ffd04a6819104b28276--gimp-3.0.0-arm64-1.dmg
==> Checking quarantine support
/usr/bin/env /usr/bin/xattr -h
/usr/bin/env /Library/Developer/CommandLineTools/usr/bin/swift -target arm64-apple-macosx15 /opt/homebrew/Library/Homebrew/cask/utils/quarantine.swift
==> Unknown support status
==> Verifying checksum for '60211ce3bd25a8458e5abd7df6e7f2c7c88c6ebdf9829ffd04a6819104b28276--gimp-3.0.0-arm64-1.dmg'
/usr/bin/env hdiutil imageinfo -format /Users/brian/Library/Caches/Homebrew/downloads/60211ce3bd25a8458e5abd7df6e7f2c7c88c6ebdf9829ffd04a6819104b28276--gimp-3.0.0-arm64-1.dmg
==> Uninstalling artifacts
==> 4 artifacts defined
#<Cask::ArtifactSet: {#<Cask::Artifact::PreflightBlock:0x000000012072f328 @cask=#<Cask gimp /opt/homebrew/Caskroom/gimp/.metadata/2.10.38,1.upgrading/20250228202809.794/Casks/gimp.rb>, @dsl_args=[], @directives={:preflight=>#<Proc:0x000000012072f3c8 /opt/homebrew/Caskroom/gimp/.metadata/2.10.38,1.upgrading/20250228202809.794/Casks/gimp.rb:33>}>, #<Cask::Artifact::App:0x00000001209a7c18 @cask=#<Cask gimp /opt/homebrew/Caskroom/gimp/.metadata/2.10.38,1.upgrading/20250228202809.794/Casks/gimp.rb>, @dsl_args=["GIMP.app"], @source_string="GIMP.app", @target_string="">, #<Cask::Artifact::Binary:0x00000001209a7948 @cask=#<Cask gimp /opt/homebrew/Caskroom/gimp/.metadata/2.10.38,1.upgrading/20250228202809.794/Casks/gimp.rb>, @dsl_args=["/opt/homebrew/Caskroom/gimp/2.10.38,1/gimp.wrapper.sh", {:target=>"gimp"}], @source_string="/opt/homebrew/Caskroom/gimp/2.10.38,1/gimp.wrapper.sh", @target_string="gimp">, #<Cask::Artifact::Zap:0x000000012072de60 @cask=#<Cask gimp /opt/homebrew/Caskroom/gimp/.metadata/2.10.38,1.upgrading/20250228202809.794/Casks/gimp.rb>, @dsl_args=[{:trash=>["~/Library/Application Support/Gimp", "~/Library/Preferences/org.gimp.gimp-2.10.plist", "~/Library/Saved Application State/org.gimp.gimp-2.10.savedState"]}], @directives={:trash=>["~/Library/Application Support/Gimp", "~/Library/Preferences/org.gimp.gimp-2.10.plist", "~/Library/Saved Application State/org.gimp.gimp-2.10.savedState"], :signal=>[]}>}>
==> Uninstalling artifact of class Cask::Artifact::PreflightBlock
==> Uninstalling artifact of class Cask::Artifact::App
==> Uninstalling artifact of class Cask::Artifact::Binary
==> Purging files for version 3.0.0,1 of Cask gimp
Error: gimp: No such file or directory @ rb_file_s_rename - (/opt/homebrew/Caskroom/gimp/2.10.38,1, /opt/homebrew/Caskroom/gimp/2.10.38,1.upgrading)
/opt/homebrew/Library/Homebrew/cask/installer.rb:517:in `rename'
/opt/homebrew/Library/Homebrew/cask/installer.rb:517:in `rename'
/opt/homebrew/Library/Homebrew/cask/installer.rb:517:in `backup'
/opt/homebrew/Library/Homebrew/cask/installer.rb:513:in `start_upgrade'
/opt/homebrew/Library/Homebrew/cask/upgrade.rb:205:in `upgrade_cask'
/opt/homebrew/Library/Homebrew/cask/upgrade.rb:123:in `block in upgrade_casks'
/opt/homebrew/Library/Homebrew/cask/upgrade.rb:122:in `each'
/opt/homebrew/Library/Homebrew/cask/upgrade.rb:122:in `upgrade_casks'
/opt/homebrew/Library/Homebrew/cmd/install.rb:262:in `run'
/opt/homebrew/Library/Homebrew/brew.rb:95:in `<main>'

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: No Cask quarantine support available: unknown reason.

Warning: The following formulae have the same name as core formulae:
  hashicorp/tap/consul-template
  hashicorp/tap/levant
  hashicorp/tap/nomad
  hashicorp/tap/packer
  hashicorp/tap/terraform
  hashicorp/tap/terraform-ls
  hashicorp/tap/vault
  hashicorp/tap/waypoint
Their taps are in use, so you must use these full names throughout Homebrew.

> brew config
HOMEBREW_VERSION: 4.4.26
ORIGIN: https://github.com/Homebrew/brew
HEAD: f1041842141f20bc701b522d4371d7843d905580
Last commit: 11 hours ago
Branch: stable
Core tap JSON: 24 Mar 13:18 UTC
Core cask tap JSON: 24 Mar 13:28 UTC
HOMEBREW_PREFIX: /opt/homebrew
HOMEBREW_CASK_OPTS: []
HOMEBREW_MAKE_JOBS: 10
Homebrew Ruby: 3.3.7 => /opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.3.7/bin/ruby
CPU: deca-core 64-bit arm_donan
Clang: 16.0.0 build 1600
Git: 2.39.5 => /Library/Developer/CommandLineTools/usr/bin/git
Curl: 8.7.1 => /usr/bin/curl
macOS: 15.3.2-arm64
CLT: 16.2.0.0.1.1733547573
Xcode: 16.2
Rosetta 2: false

Output of brew tap

> brew tap
hashicorp/tap