Cask that requires running an installer fails because the app isn't signed

[dam0vm3nt]

General troubleshooting steps

• [x] I understand that if I ignore these instructions, my issue may be closed without review.
• [x] I have retried my command with --force.
• [x] I ran brew update-reset && brew update and retried my command.
• [x] I ran brew doctor, fixed as many issues as possible and retried my command.
• [x] I have checked the instructions for reporting bugs.
• [x] I made doubly sure this is not a checksum does not match error.

Description of issue

This behavior happens whenever a package requires the execution of an installer, e.g. soapui

1. brew cask install soapui
2. the command downloads the DMG, mount it, copies the installer to the application folder then it tries to run the installer
3. the mac shows the usual "Application execution blocked because not signed" dialog
4. Open the security panel and click on "open it anyway"
5. The script rolls back without trying to execute the installer a second time

Command that failed

brew cask install <<any package that requires the execution of an installer not signed>>

Output of command with --force --verbose --debug

brew install soapui

Output of brew cask doctor

==> Homebrew Version
2.4.7-49-g0f5d9a5
==> macOS
10.15.5
==> SIP
Enabled
==> Java
14.0.2, 14.0.1, 1.8.0_202, 1.7.0_80
==> xattr issues
<NONE>
==> Gatekeeper support
Enabled
==> Homebrew Cask Install Location
<NONE>
==> Homebrew Cask Staging Location
/usr/local/Caskroom
==> Homebrew Cask Taps:
/usr/local/Homebrew/Library/Taps/homebrew/homebrew-cask (3617 casks)
/usr/local/Homebrew/Library/Taps/homebrew/homebrew-cask-versions (155 casks)
==> Contents of $LOAD_PATH
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/ruby-macho-2.2.0/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/rubocop-rspec-1.42.0/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/rubocop-performance-1.7.0/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/rexml-3.2.4/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/plist-3.5.0/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/mechanize-2.7.6/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/activesupport-6.0.3.2/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/zeitwerk-2.4.0/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/tzinfo-1.2.7/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/thread_safe-0.3.6/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/i18n-1.8.3/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/concurrent-ruby-1.1.6/lib/concurrent-ruby
/Library/Ruby/Site/2.6.0
/Library/Ruby/Site/2.6.0/universal-darwin19
/Library/Ruby/Site
/System/Library/Frameworks/Ruby.framework/Versions/2.6/usr/lib/ruby/vendor_ruby/2.6.0
/System/Library/Frameworks/Ruby.framework/Versions/2.6/usr/lib/ruby/vendor_ruby/2.6.0/universal-darwin19
/System/Library/Frameworks/Ruby.framework/Versions/2.6/usr/lib/ruby/vendor_ruby
/System/Library/Frameworks/Ruby.framework/Versions/2.6/usr/lib/ruby/2.6.0
/System/Library/Frameworks/Ruby.framework/Versions/2.6/usr/lib/ruby/2.6.0/universal-darwin19
/usr/local/Homebrew/Library/Homebrew
==> Environment Variables
LC_ALL="en_US.UTF-8"
PATH="/usr/local/Homebrew/Library/Homebrew/shims/scm:/usr/bin:/bin:/usr/sbin:/sbin"
SHELL="/usr/local/bin/zsh"

Output of brew tap

dart-lang/dart
heroku/brew
homebrew/cask
homebrew/cask-versions
homebrew/core
homebrew/services
weaveworks/tap

[dam0vm3nt]

It would be nice to have a built in mechanism that resolve this issues in a package agnostic way.

[miccal]

See https://github.com/Homebrew/homebrew-cask/issues/86020 -- you need to use the --no-quarantine flag in these circumstances.