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I've got "Automatically install new apps" checked on all my iDevices, but it hardly ever does what it says. For example, I just downloaded three new apps to my computer and then did a Sync operation on two iPads and an iPhone -- none of the new apps showed up. On the App List, they each showed the button as Install. When I pressed the Install button on the App List for each of the affected apps, they then installed on the next Sync.

Just to keep me guessing, new apps WILL occasionally install correctly, but I've never figured out what magic circumstance triggered the proper behavior.

Ideas?

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Does it download after you download any other application via any iDevice? I hardly download via iTunes as I download everything via my iPhone/iPad and they sync correctly... –  Rob Feb 15 at 10:13

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Apple is not doing very good programming lately, they have shifted their resources to making iOS look pretty. They are not enterprise ready yet and this is just one example, I have ran into this issue about 20 times and its such a time consuming task to manually click update or install on each iPad, because you can hold the command key and clicking one app will automatically highlight all, but yes the automatically install new apps checkmark should do all this for you, applause for Apple's software team on their historic buggy software releases. I am not 100% on this but make sure your restrictions allow apps to be deleted and install apps is allowed, and delete all caches in the users library, reboot, try again.. sorry if that doesnt help..

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