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I just manually deleted about 1gb of useless old version files from that folder. But I've got 966 items there and no way to going through them all, plus some of them are not even that simple to identify as being an older version of the same app since they change names.

Is there any way to automate the process? Why are they kept there in the first place?

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What version of iTunes are you running? The current iTunes automatically moves old versions of an app to the Trash bin after downloading an update. Just download an update and check your trash for changes. – hotpaw2 Jul 19 '11 at 20:34
@hotpaw2 it should always be the most updated iTunes. Right now, it's 10.3.1 right now. Those files are hanging in there for long time now. And I did see some old versions thrown away on the garbage from time to time, which made me even more surprised finding out so many not trashed out. – cregox Jul 19 '11 at 21:07
up vote 1 down vote accepted

Here's how I did it:

  1. Backup your iTunes library in case this goes wrong. ;)
  2. Move all app files from "Mobile Applications" to the Desktop.
  3. Remove all apps from the iTunes library, but pick "Keep Files".
  4. (Temporarily) enable "Copy files to iTunes Media Folder when adding to library." in the iTunes preferences.
  5. Drag the app files from your Desktop into iTunes.
  6. Unfortunately, iTunes will prompt you when it finds duplicates. But "Don't Replace" or "Replace" is preselected correctly based on which version is newer. So you can just hold the Return key down through the process.

The downside is: all apps are considered new now. So maybe disable "Automatically sync new apps" in the device sync screen before syncing.

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Isn't this going to also delete all app data? And isn't this the exact same idea from bmike? – cregox Nov 24 '11 at 23:31
It differs in that you keep all your apps, not just the ones on your device. It's less work if you have multiple devices. Not going over USB is also faster. App data of already synced apps isn't affected. – nschum Nov 25 '11 at 20:30
Haven't really tested it, since I'm not anymore using iPhone, I dun care... But I'll take your word, and this looks good enough. – cregox Feb 26 '12 at 4:14

I don't know an easy solution to change iTunes, but I do have a cleaner library by letting go. It's not exactly what you ask, but here goes anyhow.

I did one good backup of my user folder and then deleted all apps from within iTunes. Then I cleared out the folders to remove any left over / orphan app files.

Then I connected my devices one by one and just transferred the purchases. Less updates of un-needed apps and less space used.

I suppose they could pull an app from sale and I might miss out on some updates, but I'm willing to take that risk. I've still got the last version I wasn't using stored on my backup.

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good idea. I'll leave this open for little longer tho, in hope of a better one! ;) – cregox Jul 19 '11 at 1:07
now I was wondering... doesn't this delete along all app data? – cregox Nov 24 '11 at 23:33

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