Slack [re-]installation problem

[sfuerte]

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

slack gets stuck both on brew upgrade -g and brew reinstall -f slack.

That's actually the second time having issues with slack specifically, but the previous time reinstall -f did help. Apparently not this one.
All other casks and formulas updating and installing just fine.

Not that it should matter in any way. But as a side note: the system itself can be considered as a brand new. The device is just 3 weeks old, and not that it has 5-year history on it.
Interestingly, wasn't able to reproduce on my other system with quite a bit of history on it but fairly the same config (both system and app-layer wise).

Command that failed

brew upgrade -g

Output of command with --verbose --debug

> brew reinstall -f -vv --debug slack
/opt/homebrew/Library/Homebrew/brew.rb (Formulary::NullLoader): loading slack
/opt/homebrew/Library/Homebrew/brew.rb (Formulary::NullLoader): loading slack
/opt/homebrew/Library/Homebrew/brew.rb (Formulary::NullLoader): loading slack
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading slack
==> Cask::Installer#install
/opt/homebrew/Library/Homebrew/brew.rb (Cask::CaskLoader::FromAPILoader): loading slack@beta
==> Printing caveats
==> Cask::Installer#fetch
==> Downloading https://downloads.slack-edge.com/desktop-releases/mac/arm64/4.44.65/Slack-4.44.65-macOS.dmg
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.5.6\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.5\)\ 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/4.5.6\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.5\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 --fail --location --silent --head https://downloads.slack-edge.com/desktop-releases/mac/arm64/4.44.65/Slack-4.44.65-macOS.dmg
/usr/bin/env /opt/homebrew/Library/Homebrew/shims/shared/curl --disable --cookie /dev/null --globoff --show-error --user-agent Homebrew/4.5.6\ \(Macintosh\;\ arm64\ Mac\ OS\ X\ 15.5\)\ curl/8.7.1 --header Accept-Language:\ en --retry 3 --fail --location --silent --head --request GET --http1.1 https://downloads.slack-edge.com/desktop-releases/mac/arm64/4.44.65/Slack-4.44.65-macOS.dmg
Already downloaded: $HOME/Library/Caches/Homebrew/downloads/7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.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
==> Quarantine is available.
==> Verifying Gatekeeper status of $HOME/Library/Caches/Homebrew/downloads/7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.dmg
/usr/bin/env /usr/bin/xattr -p com.apple.quarantine $HOME/Library/Caches/Homebrew/downloads/7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.dmg
==> $HOME/Library/Caches/Homebrew/downloads/7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.dmg is quarantined
==> Verifying checksum for '7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.dmg'
/usr/bin/env tar --list --file $HOME/Library/Caches/Homebrew/downloads/7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.dmg
/usr/bin/env hdiutil imageinfo -format $HOME/Library/Caches/Homebrew/downloads/7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.dmg
==> Installing Cask slack
==> Cask::Installer#stage
==> Extracting primary container
==> Using container class UnpackStrategy::Dmg for $HOME/Library/Caches/Homebrew/downloads/7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.dmg
/usr/bin/env hdiutil attach -plist -nobrowse -readonly -mountrandom /private/tmp/homebrew-dmg20250610-41521-vdcxvh $HOME/Library/Caches/Homebrew/downloads/7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.dmg
/usr/bin/env hdiutil convert -format UDTO -o /private/tmp/homebrew-dmg20250610-41521-vdcxvh/7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.cdr $HOME/Library/Caches/Homebrew/downloads/7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.dmg
/usr/bin/env hdiutil attach -plist -nobrowse -readonly -mountrandom /private/tmp/homebrew-dmg20250610-41521-vdcxvh /private/tmp/homebrew-dmg20250610-41521-vdcxvh/7f643b2591cc0e2d3555ef03a0fe0b68f7beff62903131a8752921f3cb39670e--Slack-4.44.65-macOS.cdr
/usr/bin/env find . -print0
/usr/bin/env mkbom -s -i /private/tmp/20250610-41521-nl347x.list -- /private/tmp/20250610-41521-pla2a6.bom
/usr/bin/env ditto --bom /private/tmp/20250610-41521-pla2a6.bom -- /private/tmp/homebrew-dmg20250610-41521-vdcxvh/dmg.t49brq /private/tmp/homebrew-unpack-20250610-41521-y64aco
/usr/bin/env diskutil info -plist /private/tmp/homebrew-dmg20250610-41521-vdcxvh/dmg.t49brq
/usr/bin/env diskutil eject /private/tmp/homebrew-dmg20250610-41521-vdcxvh/dmg.t49brq

^C==> Purging files for version 4.44.65 of Cask slack
Error: Read-only file system @ apply2files - /private/tmp/homebrew-dmg20250610-41521-vdcxvh/dmg.t49brq/.background/dmgbackground.tiff
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2332:in 'File.unlink'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2332:in 'block in FileUtils::Entry_#remove_file'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2337:in 'FileUtils::Entry_#platform_support'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2331:in 'FileUtils::Entry_#remove_file'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2320:in 'FileUtils::Entry_#remove'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:1453:in 'block in FileUtils.remove_entry'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2379:in 'block (2 levels) in FileUtils::Entry_#postorder_traverse'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2379:in 'block (2 levels) in FileUtils::Entry_#postorder_traverse'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2379:in 'block (2 levels) in FileUtils::Entry_#postorder_traverse'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2383:in 'FileUtils::Entry_#postorder_traverse'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2378:in 'block in FileUtils::Entry_#postorder_traverse'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2377:in 'Array#each'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2377:in 'FileUtils::Entry_#postorder_traverse'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2378:in 'block in FileUtils::Entry_#postorder_traverse'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2377:in 'Array#each'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2377:in 'FileUtils::Entry_#postorder_traverse'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2378:in 'block in FileUtils::Entry_#postorder_traverse'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2377:in 'Array#each'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:2377:in 'FileUtils::Entry_#postorder_traverse'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/fileutils.rb:1451:in 'FileUtils.remove_entry'
/opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/lib/ruby/3.4.0/tmpdir.rb:114:in 'Dir.mktmpdir'
/opt/homebrew/Library/Homebrew/unpack_strategy/dmg.rb:199:in 'UnpackStrategy::Dmg#mount'
/opt/homebrew/Library/Homebrew/unpack_strategy/dmg.rb:188:in 'UnpackStrategy::Dmg#extract_to_dir'
/opt/homebrew/Library/Homebrew/unpack_strategy.rb:149:in 'UnpackStrategy#extract'
/opt/homebrew/Library/Homebrew/unpack_strategy.rb:164:in 'block in UnpackStrategy#extract_nestedly'
/opt/homebrew/Library/Homebrew/mktemp.rb:90:in 'Mktemp#run'
/opt/homebrew/Library/Homebrew/unpack_strategy.rb:161:in 'UnpackStrategy#extract_nestedly'
/opt/homebrew/Library/Homebrew/cask/installer.rb:284:in 'Cask::Installer#extract_primary_container'
/opt/homebrew/Library/Homebrew/cask/installer.rb:124:in 'Cask::Installer#stage'
/opt/homebrew/Library/Homebrew/cask/installer.rb:153:in 'Cask::Installer#install'
/opt/homebrew/Library/Homebrew/cask/reinstall.rb:29:in 'block in Cask::Reinstall.reinstall_casks'
/opt/homebrew/Library/Homebrew/cask/reinstall.rb:26:in 'Array#each'
/opt/homebrew/Library/Homebrew/cask/reinstall.rb:26:in 'Cask::Reinstall.reinstall_casks'
/opt/homebrew/Library/Homebrew/cmd/reinstall.rb:176:in 'Homebrew::Cmd::Reinstall#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: Some installed formulae are missing dependencies.
You should `brew install` the missing dependencies:
  brew install kubernetes-cli

Run `brew missing` for more details.

# that is by choice and has nothing to do with 'slack'
# note on this one, 'kubectl' is part of 'docker' and 'kubectx' could've been more relaxed on the dependency list
> brew missing
kubectx: kubernetes-cli


> brew config
HOMEBREW_VERSION: 4.5.6
ORIGIN: https://github.com/Homebrew/brew
HEAD: 7b4ef99fed96966269ee35994407fa4c06097a4d
Last commit: 16 hours ago
Branch: stable
Core tap JSON: 10 Jun 14:56 UTC
Core cask tap JSON: 10 Jun 14:56 UTC
HOMEBREW_PREFIX: /opt/homebrew
HOMEBREW_CASK_OPTS: []
HOMEBREW_MAKE_JOBS: 14
HOMEBREW_NO_ANALYTICS: set
Homebrew Ruby: 3.4.4 => /opt/homebrew/Library/Homebrew/vendor/portable-ruby/3.4.4/bin/ruby
CPU: 14-core 64-bit arm_brava
Clang: 17.0.0 build 1700
Git: 2.49.0 => /opt/homebrew/bin/git
Curl: 8.7.1 => /usr/bin/curl
macOS: 15.5-arm64
CLT: 16.4.0.0.1.1747106510
Xcode: N/A
Rosetta 2: false

Output of brew tap

> brew tap

# nada, i.e. returns nothing

[sfuerte]

I guess all my attempts and more details towards the root cause?

> mount
...
/dev/disk4s1 on /private/tmp/homebrew-dmg20250610-38629-iugmtj/dmg.Pdbv4Z (hfs, local, nodev, nosuid, read-only, noowners, quarantine, nobrowse, mounted by $USER)
/dev/disk6s1 on /private/tmp/homebrew-dmg20250610-40208-nx5qg4/dmg.XBHglR (hfs, local, nodev, nosuid, read-only, noowners, nobrowse, mounted by $USER)
/dev/disk7s1 on /private/tmp/homebrew-dmg20250610-41521-vdcxvh/dmg.t49brq (hfs, local, nodev, nosuid, read-only, noowners, nobrowse, mounted by $USER)
/dev/disk5s1 on /private/tmp/homebrew-dmg20250610-42615-elz4qw/dmg.3tRY7A (hfs, local, nodev, nosuid, read-only, noowners, nobrowse, mounted by $USER)
/dev/disk8s1 on /private/tmp/homebrew-dmg20250610-44701-rko9ju/dmg.FP5mwD (hfs, local, nodev, nosuid, read-only, noowners, nobrowse, mounted by $USER)

UPD, forgot to mention, doing the below runs the app itself with no problem:

> rm -Rf /Applications/Slack.app
> cp -R /private/tmp/homebrew-dmg20250610-41521-vdcxvh/dmg.t49brq/Slack.app /Applications/