Full brew and brew cask upgrade cycle in https://github.com/benjaminoakes/maid

rules.rb

#
# Full brew and brew cask upgrade cycle in https://github.com/benjaminoakes/maid
#
Maid.rules do

  ### Homebrew:

  rule 'Updating brew formulas' do
    log(`brew update`)
  end

  rule 'Upgrading installed brew formulas' do
    log(`brew upgrade -all`)
  end

  rule 'Cleaning brew' do
    log(`brew cleanup`)
  end

  #Get all installed brew casks
  installedCasks = (`brew cask list`).split()

  # Upgrade casks, that have a version number other than latest
  # Inspiration from https://github.com/caskroom/homebrew-cask/issues/4678#issuecomment-77692503
  rule 'Update brew casks' do
    updateHappened = false

    installedCasks.each do |cask|
      needToInstall = system("brew cask info #{cask} |grep -qF 'Not installed'")
      if needToInstall
        updateHappened = true
        log("New Version of homebrew cask #{cask}, will install it")
        log(`brew cask install #{cask}`)
      end
    end

    log('No brew cask updated') unless updateHappened
  end

  # Delete old cask versions
  # Inspiration from https://gist.github.com/orangeudav/26a8752ae54a169b8516
  rule 'Clean brew casks' do

    log(`brew cask cleanup`)

    installedCasks.each do |cask|

      # Get installed version folders for each installed cask
      versions = dir("/opt/homebrew-cask/Caskroom/#{cask}/*")

      # Jump to next if only one version is installed
      next if versions.size == 1

      # Sort version folders by creation date
      versions.sort_by! do |item|
        created_at(item)
      end

      # Remove newest version folder from list
      currVer = versions.pop
      log("We won't delete newest version (#{currVer}) of #{cask}")

      # Trash all remaining versions
      versions.each do |version|
        trash(version)
      end

    end
  end

end

How do you deal with upgrades that need sudo privileges (and prompt for password)?

Hi! Thanks for putting together this awesome script. I've just installed maid and used it for the first time this morning, and the two seem to work really well together and did exactly the job they advertised :-)

I added two flags to allow the user to choose whether this script should upgrade the software before clean-up or not. Within the scientific community we typically retain older versions of software for quite some time until we're sure that an upgrade won't cause any compatibility issues or break any core functionality. That is to say that full manual control over upgrades is a must for me (and probably many others). Feel free to merge my fork if you desire.

This script periodically removes the cask-installed Firefox.