The new flow is described in the section "2018 update" above. #Brew update cask upgrade#The next paragraphs are deprecated since 2018, when the command brew cask upgrade has been implemented. You'll need this for automation on the third step. The option -quiet tells it to show only the package names, without versions. This command shows the list of outdated programs managed by Cask, together with the installed version and the new version. The second step is to run brew cask outdated. #Brew update cask update#You can use any of them brew update is preferred because it is shorter. Homebrew Cask provides the sub-command brew cask update but it is just an alias of brew update. #Brew update cask code#It updates Homebrew code and the taps (a tap is a repository of programs managed by Homebrew). The process is slightly different than the above. Upgrading all outdated graphical programs is not that straightforward at the moment. Replace with the package name displayed by brew outdated. In this case you can pick the programs you want to upgrade and run brew upgrade for each program you want to update. brew outdated only lists the outdated installed programs it is useful if you do the upgrade manually and you don't want to upgrade everything. brew upgrade internally calls brew update if the last update happened too much time in the past. The brew update and brew outdated steps are optional. # Upgrade all the outdated programs and their dependencies Upgrading all outdated programs installed with brew (command line programs) is easy: # Tell Homebrew to update itself and its taps (repositories of programs) The Homebrew itself manages only command line applications. It started as an extension of the original Homebrew it is now an integrated command of brew. Homebrew Cask is a component of Homebrew that allows management of graphical applications. You are mixing brew commands with brew cask commands and it doesn't work this way. Using it ensures your system is up to date with the additional cost of reinstalling some applications that are not outdated. The command brew cask upgrade also accepts the -greedy option (internally it uses brew cask outdated to find the list of packages to upgrade). Those having latest as their version cannot be checked and are always listed, those marked as auto-updateable are checked and listed only if they are outdated indeed. This command includes in its output the casks mentioned above. To list them one have to add the -greedy option in the command line of brew cask outdated: $ brew cask outdated -greedy These two categories of casks are not listed by brew cask outdated. Some casks mark themselves as auto-updateable while others use the keyword latest as their version. Sometimes, brew cask outdated does not list all the outdated casks. It can replace the for block in the script that now becomes: # Upgrade Homebrew and the information about formulas It also works without arguments and upgrades all the casks displayed by brew cask outdated. In the meantime, the brew cask upgrade command has been implemented and can be used instead of brew cask reinstall in the script provided in the original answer. The original answer and the 2018 update are kept for historical reasons. It also supports the options listed above for brew outdated and operates accordingly. The third command ( brew upgrade) upgrades the packages listed by brew outdated. Add -greedy to the command line to include in its output the casks that are marked as "auto-updateable". Add -formulae or -casks to the command line to limit the command scope to formulae or casks. The second command ( brew outdated) lists the outdated installed formulae and casks. The first command ( brew update) gets from the Homebrew servers the information about the most recent versions of the available formulae and casks. There is a unified flow now for both formulae and casks: brew update The cask command has been completely removed from Homebrew in version 2.6.0, released in December 2020. To limit their scope to only formulae or casks add the -formula or -cask option to the command line. The core commands now operate on both formulae and casks. During 2020 the sub-commands of the cask command were gradually integrated into the core of Homebrew and were deprecated.
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