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Why can't I update an app >20 meg on 3G?

It's just the Apple way.

If you want to overcome the restriction jailbreak your device and install "3G Unrestrictor". This lets you specify any app to operate over 3G as though it was on wi-fi, thus removing any limits imposed by Apple.
 
When AT&T originally contracted as the exclusive carrier for the iPhone, this was a condition of the contract.

It has stuck...

Complain to Apple through the feedback form on their website. They can make this a carrier setting and not global.
 

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