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This seems to be a known Droid issue. I've seen many posts concerning this very thing. Seems as though the only thing you can do after headphone use is power the phone off and back on and the sound (speakers) will start working again. Weird, huh? :icon_rolleyes:
it only does that for the stock music player, and even than if you have a task killer, kill the music player and start it back up and it will play thru your speakers. But if your listening to lets say rhapsody and unplug your headphones it will continue playing thru your speakers.