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I would like iTunes to always download free updates for any applications that I have on my iPhone.

Is that possible?

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up vote 4 down vote accepted

As far as I know, although both iTunes and the iPhone/Pad check automatically for updates, you have to manually start the process.

Yes, I know it’s a bad idea, because we almost always click “download all”. Even if you tell iTunes to remember your password, it won’t start the download automatically whenever there are updates. I have been looking for a way to do this since the iPhone 1G and haven’t come across a solution yet.

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It's a 'good' idea, in that most updates install new functionality. The thinking is that the end user should see and manually approve if an app has added 'Share all my files with everyone on the internet' functionality', otherwise, anything could be added to initially innocuous looking apps. (I'm slightly 'odd' in that I read and enjoy(!) every app's update notes). – Jon Hadley Oct 19 '10 at 12:42
@Jon although I understand that, in practice, nobody does it. Plus the fact that watching the “changelog” for each app is impractical (and requires back and forth of ‘slow loadings’). So we usually “Update All” and get over with. :) – Martín Marconcini Oct 19 '10 at 12:50

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