MacRumors got a tip that Apple inadvertently revealed an over-the-air app update feature for iOS in iTunes. This would indicate that such a feature will be available in iOS 5, which will be announced Monday at WWDC. Apple could also be bringing system updates to iOS which would finally allow users to cut the cord entirely.
It also suggests that there is an Automatic Download setting for other items besides apps. Apple has been rumored to be making a push into over-the-air updates as well as some sort of wireless syncing. Rumors of AirPort Extreme and Time Capsule updates have also hinted at such a feature.
via Mac Rumors