brew upgrade uninstalls casks with installer manual:

[yurii-kolesnykov-better]

brew config output

HOMEBREW_VERSION: 3.1.6-22-g2b9fd54
ORIGIN: https://github.com/Homebrew/brew
HEAD: 2b9fd5460e357b6638944f4f89917a669a5af68c
Last commit: 8 hours ago
Core tap ORIGIN: https://github.com/Homebrew/homebrew-core
Core tap HEAD: a331500c25c416ba709c811a248c4649aca4b5c7
Core tap last commit: 6 hours ago
Core tap branch: master
HOMEBREW_PREFIX: /usr/local
HOMEBREW_CASK_OPTS: []
HOMEBREW_EDITOR: subl -w
HOMEBREW_GITHUB_API_TOKEN: set
HOMEBREW_MAKE_JOBS: 6
Homebrew Ruby: 2.6.3 => /System/Library/Frameworks/Ruby.framework/Versions/2.6/usr/bin/ruby
CPU: hexa-core 64-bit kabylake
Clang: 12.0.5 build 1205
Git: 2.31.1 => /usr/local/bin/git
Curl: 7.64.1 => /usr/bin/curl
macOS: 11.4-x86_64
CLT: 12.5.0.22.9
Xcode: 12.5

brew doctor output

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: The filesystem on /System/Volumes/Data appears to be case-sensitive.
The default macOS filesystem is case-insensitive. Please report any apparent problems.

Warning: Putting non-prefixed coreutils in your path can cause GMP builds to fail.

Warning: You have unlinked kegs in your Cellar.
Leaving kegs unlinked can lead to build-trouble and cause formulae that depend on
those kegs to fail to run properly once built. Run `brew link` on these:
  bash-completion
  gnupg

• I ran brew update and am still able to reproduce my issue.
• I have resolved all warnings from brew doctor and that did not fix my problem.

What were you trying to do (and why)?

I'm greedy, so I run brew upgrade --fetch-HEAD --greedy once per day, but I have one cask with version :latest and installer manual:, it's battle-net, so I need to reinstall it manually every time I want to use it. I wanted to report this a long time ago, but had no time for this until I saw an error in installed today. It may be related to the fact that I use beta branch of Battle.net and stable installer didn't handle configs and caches from newer version.

I understand that this particular cask and my habits is a bad example and a corner case, but I still consider this to be a bug.

What happened (include all command output)?

brew install battle-net
==> Caveats
If you pick an installation directory other than /Applications when installing this cask, you will need to uninstall it manually

==> Downloading https://www.battle.net/download/getInstallerForGame?os=mac&locale=enUS&version=LIVE&gameProgram=BATTLENET_APP
==> Downloading from https://eu.battle.net/download/getInstaller?os=mac&installer=Battle.net-Setup.zip
            -=#=-   #    #     #                                              
Warning: No checksum defined for cask 'battle-net', skipping verification.
==> Installing Cask battle-net
To complete the installation of Cask battle-net, you must also
run the installer at:
  /usr/local/Caskroom/battle-net/latest/Battle.net-Setup.app
🍺  battle-net was successfully installed!
➜  ~ open /usr/local/Caskroom/battle-net/latest/Battle.net-Setup.app
➜  ~ brew upgrade battle-net
==> Upgrading 1 outdated package:
battle-net latest -> latest
==> Upgrading battle-net
==> Caveats
If you pick an installation directory other than /Applications when installing this cask, you will need to uninstall it manually

==> Downloading https://www.battle.net/download/getInstallerForGame?os=mac&locale=enUS&version=LIVE&gameProgram=BATTLENET_APP
==> Downloading from https://eu.battle.net/download/getInstaller?os=mac&installer=Battle.net-Setup.zip
              -=O=-#    #     #     #                                         
Warning: No checksum defined for cask 'battle-net', skipping verification.
==> Removing files:
/Applications/Battle.net.app
To complete the installation of Cask battle-net, you must also
run the installer at:
  /usr/local/Caskroom/battle-net/latest/Battle.net-Setup.app
==> Purging files for version latest of Cask battle-net
🍺  battle-net was successfully upgraded!

What did you expect to happen?

Battle.net shouldn't be removed.

Step-by-step reproduction instructions (by running brew commands)

brew install battle-net
open /usr/local/Caskroom/battle-net/latest/Battle.net-Setup.app
<install it>
brew upgrade battle-net

[yurikoles]

Whoops, work account. That was me.

[yurikoles]

I think that app being lost after brew upgrade is unexpected and bad UX for users.

[vitorgalvao]

I understand that this particular cask and my habits is a bad example and a corner case

You’re right.

but I still consider this to be a bug.

A bug is unexpected behaviour. This is expected, it just doesn’t work like you want. installer manual: software are a bad experience in general, you should complain upstream. Making workarounds instead of fixing bad software is what leads to the current state of the world’s software being held with duct tape.

If you don’t want to try to convince upstream, then don’t use --greedy, or install this outside of HBC, or make your own local workaround, or find a way for this to be installed without requiring an app installer.