Repeated Password Prompts with PowerShell

[channyein87]

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

Everytime upgrading or uninstalling PowerShell, there is a repeated password prompts to continue and have to enter the password multiple times.

Command that failed

brew upgrade powershell
brew uninstall powershell
brew uninstall powershell --force
brew cask uninstall powershell --force --verbose --debug

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

==> Uninstalling Cask powershell
==> Uninstalling packages:
com.microsoft.powershell
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Sorry, try again.
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Sorry, try again.
Password:
Password:
Password:
Password:
Password:
Sorry, try again.
Password:
Password:
Password:
Password:
Password:
Sorry, try again.
Password:
Sorry, try again.
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Sorry, try again.
Password:
Password:
Sorry, try again.
Password:
Password:
Sorry, try again.
Password:
Password:
Password:
Password:
Password:
Password:
Sorry, try again.
Password:
Password:
Sorry, try again.
Password:
Password:
Sorry, try again.
Password:
Sorry, try again.
Password:
Password:
Password:
Sorry, try again.
Password:
Sorry, try again.
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
Password:
==> Purging files for version 7.0.2 of Cask powershell

Output of brew cask doctor

==> Homebrew Version
2.4.5
==> macOS
10.15.5
==> SIP
Enabled
==> Java
13.0.2
==> 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 (3609 casks)
/usr/local/Homebrew/Library/Taps/homebrew/homebrew-cask-fonts (1547 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-1.41.0/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-2.3.1/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="/bin/bash"

Output of brew tap

aws/tap
homebrew/cask
homebrew/cask-fonts
homebrew/core
teamookla/speedtest
warrensbox/tap

[vitorgalvao]

Cannot reproduce on a clean VM and this is a very popular cask with no further reports on the matter. The issue is on your side.

My guess would be that you’ve setup sudo to ask for the password every time, and as the cask may be needing it to remove every file, you get the repeated prompt. Nothing we can do about that.