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I am having issues with watching video I already have on my Droid. I can watch youtube but any video that is sent to me or video from a website that isn't youtube it gives me an error message. This started after the 2.2 update.
You probably need to convert the file to something that the Droid can play. I do remember some comments about this last year when we went to 2.2 but unfortunately I don't know what the fix is.