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When will EVO ship with 2.2?

HTC are not in the market to make their software compatible with unofficial ROMs.
Eventually shipped from the factory phones will have 2.2 updated as well as any other fixes that may come up.

as to the OP, there is no hassle involved with updating, its all done automatically with no human intervention other than giving it the go ahead to start the update.
 
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my replacement evo just came in today (had a slight screen separation and light bleeding out), and it had 2.1... i am not sure if i will regret it, but i am updating it right now with 2.2. i like having flash on the internet,but i am annoyed by pandora pausing when navigating. hopefully froyo will be fixed soon.
 
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