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I looked around for this and couldn't find it. Before venturing into coding it, I thought I'd ask…

I regularly update my mac via terminal with brew, macports, pip, yarn, etc. So I started reinstalling my apps via brew cask so they get regularly updated. It's pretty mechanical, and I'm sure there's a way to automate it. All it'd need to do is ls the apps in the Applications folder, compare it to the brew cask list, and brew cask --force install those not already there. A more rounded script would use brew search and ask the user to pick and confirm if results were ambivalent.

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Sorted!

cd /Applications
brew cask list -1 > apps.txt
brew search --casks > casks.txt
for f in *.app do
    if grep -Fixq ${${f%.*}// /-} casks.txt && ! grep -Fixq ${${f%.*}// /-} apps.txt
        then HOMEBREW_NO_AUTO_UPDATE=1 brew cask install --force ${${f%.*}// /-}
    fi
done
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