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> Quite a few of the apps I use (iTerm2, ST3, Chrome, Adium, etc.) update themselves periodically. I wonder how Cask deals with that?

Sparkle-based self-updating apps will self-update in place. For apps like that, the current policy is to have a Cask version of 'latest', and letting the apps self update.

I've been doing this for some time and I've found it works out AOK. It's nice to be able to click the "Update & Relaunch" and know I'm not messing anything up. :)

Apple actually has a few ways of making a list of installed apps, as shown in System Information. More on this buried in http://stackoverflow.com/questions/2765063/how-can-i-discove... ... My fav. tricks tend to be all the nice -xml commands Apple offers. Oh ... and "Installations" probably lists all the receipts from running graphical installers, this being different from drag-and-drop .app lists which you can also find.

> If there was some way to let Cask scan your system and know that I've already installed google-chrome and adium that would be cool.

I'd love to see this too - I'm keen on the idea of Cask, but at the moment my system is fairly complete.