Manually checking each app for updates is tedious and error-prone. Here’s how to automate the process so your Mac always runs the latest versions.

Homebrew Cask — One Command to Rule Them All

If you installed apps via Homebrew Cask, updating everything is a single command:

brew upgrade --cask --greedy

The --greedy flag checks for updates in apps that use their own auto-updater (like Chrome or VS Code), not just those managed by Homebrew.

Set Up Automatic Updates

Create a simple launchd job to run updates weekly:

brew autoupdate start --upgrade-interval 7

This runs brew update and brew upgrade automatically every 7 days in the background.

Mac App Store Apps

Apps from the Mac App Store update automatically if you enable it:

  • Open System Settings → App Store
  • Enable Automatic Updates

Apps with Built-in Updaters

Many apps (Chrome, Firefox, VS Code, Discord) check for updates on launch and install them silently. There’s nothing you need to do — just close and reopen the app occasionally.

Check What’s Out of Date

To see which of your Homebrew-installed apps need updates:

brew outdated --cask --greedy

This lists every cask with a newer version available, without installing anything.

The Complete Update Routine

Once a week, run these three commands:

brew update && brew upgrade
brew upgrade --cask --greedy
softwareupdate --install --all

That covers Homebrew formulas, Homebrew casks, and macOS system updates — all in 30 seconds.