Cask free-gpgmail: Upgrade fails, leaves half-uninstalled state

[jl-stellar]

Output of brew config

HOMEBREW_VERSION: 4.0.10
ORIGIN: https://github.com/Homebrew/brew
HEAD: cf6614b50eac1c9f4bf386dc6989f0d443148df8
Last commit: 3 days ago
Core tap origin: https://github.com/Homebrew/homebrew-core
Core tap HEAD: 9984d2778949b441beeb63010366aefd12faa2eb
Core tap last commit: 4 weeks ago
Core tap branch: master
Core tap JSON: 29 Mar 14:09 UTC
HOMEBREW_PREFIX: /usr/local
HOMEBREW_CASK_OPTS: []
HOMEBREW_DISPLAY: /private/tmp/com.apple.launchd.owDppHPjtM/org.xquartz:0
HOMEBREW_MAKE_JOBS: 8
Homebrew Ruby: 2.6.8 => /usr/local/Homebrew/Library/Homebrew/vendor/portable-ruby/2.6.8_1/bin/ruby
CPU: octa-core 64-bit kabylake
Clang: 14.0.0 build 1400
Git: 2.37.1 => /Applications/Xcode.app/Contents/Developer/usr/bin/git
Curl: 7.86.0 => /usr/bin/curl
macOS: 13.2.1-x86_64
CLT: N/A
Xcode: 14.2

Output of 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: Unbrewed dylibs were found in /usr/local/lib.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae, and may need to be deleted.

Unexpected dylibs:
  /usr/local/lib/libusb-1.0.0.dylib
  /usr/local/lib/libusb-1.0.dylib

Warning: Unbrewed header files were found in /usr/local/include.
If you didn't put them there on purpose they could cause problems when
building Homebrew formulae, and may need to be deleted.

Unexpected header files:
  /usr/local/include/node/v8-inspector-protocol.h
  /usr/local/include/node/v8-inspector.h
  /usr/local/include/python2.7/zope.proxy/proxy.h
  /usr/local/include/python3.7m/greenlet/greenlet.h

Description of issue

I wanted to upgrade free-gpgmail so I ran brew update and brew upgrade.
The upgrade failed:

free-gpgmail 7,2022.2.1, -> 7.1,2023.1,
==> Upgrading free-gpgmail
==> Downloading https://github.com/Free-GPGMail/Free-GPGMail/releases/download/v2023.1/Free-GPGMail_7.1-2023.1.mailbundle.zip
==> Downloading from https://objects.githubusercontent.com/github-production-release-asset-2e65be/273332178/2c3a2b88-63ff-4769-9cb2-19b12d7d0223?X-Amz-Algorithm=AWS4-HMAC-SHA256&X-Amz-Credential=AKIAIWNJYAX4CSVEH5
######################################################################## 100.0%
All formula dependencies satisfied.
==> Removing files:
~/Library/Mail/Bundles/Free-GPGMail_7.mailbundle
Password:
==> Purging files for version 7.1,2023.1, of Cask free-gpgmail
Error: free-gpgmail: It seems the Generic Artifact source '/Users/jl-stellar/Library/Mail/Bundles/Free-GPGMail_7.mailbundle' is not there.

Apple Mail was still running at that point. The plugin was still there and usable. However, after quitting and restarting the app, the plugin was gone (both its settings tab and the entry in the plugin list under "Manage Plugins").
Retrying the brew upgrade process returned the same error.
Running brew install --cask free-gpgmail returned

Warning: Cask 'free-gpgmail' is already installed.

What finally worked, was brew reinstall --cask free-gpgmail. It ran successfully and after a restart of Apple Mail, the plugin was once again available in the plugin list and could be activated successfully.

I was able to reproduce this on a colleague's MacBook, so I assume it is not entirely specific to my machine/installation. The maintainer of free-gpgmail stated that this is an issue of the cask, not the software itself (which sounds reasonable). However, the requirements for submitting an issue to homebrew-cask are so high that this didn't qualify.

What do you guys think?

Relevant casks

free-gpgmail

[papukj]

I had the same issue and solved by reinstalling the plugin.

[ekkis]

I removed and upon reinstall I still get the error:

~ $ brew remove free-gpgmail
==> Uninstalling Cask free-gpgmail
==> Removing files:
~/Library/Mail/Bundles/Free-GPGMail_6.mailbundle
==> Purging files for version 6,2021.3.1, of Cask free-gpgmail

then

~ $ brew install free-gpgmail
==> Upgrading 1 outdated package:
free-gpgmail 6,2021.3.1, -> 7.2,2023.3,
==> Upgrading free-gpgmail
==> Downloading https://github.com/Free-GPGMail/Free-GPGMail/releases/download/v2023.3/Free-GPGMail_7.2-2023.3.ma
Already downloaded: /Users/ekkis/Library/Caches/Homebrew/downloads/ad5e87ef41ed16a8e2011b4f70d18684ba6da94a04aa359bdd474b31aa1226dc--Free-GPGMail_7.2-2023.3.mailbundle.zip
All formula dependencies satisfied.
==> Removing files:
~/Library/Mail/Bundles/Free-GPGMail_6.mailbundle
==> Purging files for version 7.2,2023.3, of Cask free-gpgmail
Error: free-gpgmail: It seems the Generic Artifact source '/Users/ekkis/Library/Mail/Bundles/Free-GPGMail_6.mailbundle' is not there.

on OSX 13.6.1

[bnavigator]

The formula should probably be changed to install into the correct Homebrew prefix and check that no other installation paths interfere (See e.g. Free-GPGMail/Free-GPGMail#82)