Homebrew-cask: Emacs 27.1 upgrade results in "“Emacs.app” can’t be opened because Apple cannot check it for malicious software."

[dgr]

General troubleshooting steps

Upgrade to Emacs 27.1 cask via homebrew from 26.3 on MacOS Catalina 10.15.6.

Description of issue

Trying to run emacs from either the command line or via clicking on icon in Launchpad or dock results in error dialog with message:
"“Emacs.app” can’t be opened because Apple cannot check it for malicious software."

Command that failed

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

Can't even reach this point. MacOS Catalina won't even run it.

Output of brew cask doctor

==> Homebrew Version
2.4.11-5-g3eba477
==> macOS
10.15.6
==> SIP
Enabled
==> Java
11.0.8
==> Homebrew Cask Staging Location
/usr/local/Caskroom
==> Homebrew Cask Taps:
/usr/local/Homebrew/Library/Taps/homebrew/homebrew-cask (3638 casks)
/usr/local/Homebrew/Library/Taps/graalvm/homebrew-tap (4 casks)
/usr/local/Homebrew/Library/Taps/adoptopenjdk/homebrew-openjdk (37 casks)
==> $LOAD_PATHS
/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-1.7.1/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/patchelf-1.2.0/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/../ruby/2.6.0/gems/elftools-1.1.2/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/bindata-2.4.8/lib
/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-1.8.5/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/concurrent-ruby-1.1.7/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
==> Cask Environment Variables:
BUNDLE_PATH
CHRUBY_VERSION
GEM_HOME
GEM_PATH
HOMEBREW_CASK_OPTS
LC_ALL
PATH
RBENV_VERSION
RUBYLIB
RUBYOPT
RUBYPATH
SHELL

Output of brew tap

adoptopenjdk/openjdk
clojure/tools
graalvm/tap
heroku/brew
homebrew/cask
homebrew/core

[BrendanLeber]

I'm having the same issue.

Output from brew cask doctor

==> Homebrew Version
2.4.11
==> macOS
10.15.6
==> SIP
Enabled
==> Java
N/A
==> Homebrew Cask Staging Location
/usr/local/Caskroom
==> Homebrew Cask Taps:
/usr/local/Homebrew/Library/Taps/homebrew/homebrew-cask (3638 casks)
==> $LOAD_PATHS
/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-1.7.1/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/patchelf-1.2.0/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/../ruby/2.6.0/gems/elftools-1.1.2/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/bindata-2.4.8/lib
/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-1.8.5/lib
/usr/local/Homebrew/Library/Homebrew/vendor/bundle/bundler/../ruby/2.6.0/gems/concurrent-ruby-1.1.7/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
==> Cask Environment Variables:
BUNDLE_PATH
CHRUBY_VERSION
GEM_HOME
GEM_PATH
HOMEBREW_CASK_OPTS
LC_ALL
PATH
RBENV_VERSION
RUBYLIB
RUBYOPT
RUBYPATH
SHELL

Output from brew tap

d12frosted/emacs-plus
filippo.io/age
homebrew/cask
homebrew/core
nvie/tap
universal-ctags/universal-ctags

[miccal]

Does this issue persist if you run brew cask reinstall emacs --no-quarantine?

[dgr]

@miccal, yes, that seems to work. Thank you. Is there a way that this can be automated, such that it "just works" ?

[miccal]

@dgr not at this stage -- please see the discussion about this in https://github.com/Homebrew/homebrew-cask/issues/70798.

[vitorgalvao]

It’s working as intended from macOS security features.

Is there a way that this can be automated, such that it "just works" ?

Set HOMEBREW_CASK_OPTS=--no-quarantine in your shell’s startup files. You do so at your own risk.

[dgr]

OK, thanks. I read through #70798 and I think I get the high level sense of what’s going on. Yea, no easy solutions. Apple has made a hash of it, it seems. Now that I’ve bumped into it, I know what to do. It startled me yesterday when I did the upgrade and it suddenly wouldn’t run.