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This latest bit is still unconfirmed, however it would appear as if Apple is planning to begin charging users that re-download an app over-the-air on iPhone OS 3.0.

As it currently appears, iPhone users who purchase (and pay for) and application may end up being charged a second time for that same app. That is, assuming they delete it from their iPhone and then make an attempt to download it using an over-the-air connection. The reason behind this logic remains a mystery, however some are speculating that it has to do with account management and restricting users from being able to share apps with friends.

As of now, once you pay for an app, you are able to delete it and re-download it without having any additional charges. Let’s hope that this is one item that does not show up in the final version of iPhone OS 3.0. Of course, you could (as the pop-up alert states) always re-download the app on your computer using iTunes.

[The iPhone Blog]