Oh this is a thorn in my side and hate Motorola for it. The audio ports in Motorola Droids keep failing on me after a few months. Droid 1, after a few months the port would crackle with my headsets. Then eventually would stop hearing unless I jiggled the wires. Eventually I would lose 90% of the port's functionality. Same thing happened on my Droid 3. Droid 3 lasted even less even though I was more careful with my headsets. I use good (expensive) Bose headsets. I would listen while I walk, connect to car's Aux port, or sit in bed. Not a hell of a lot of plugging in and out acually! Yet these jacks go bad fast! By brother abuses his jack on his iPhones and gets ZERO problems (all three iphones).
Thank goodness my car has bluetooth audio and I can listen to my stuff that way. My droid 3 port is utterly useless now.
I have a very very bad experience with Motorola headphone jacks. Not to mention the voice commands suck on Motorola, but that's another topic.