Ok, so I am using Skull Candy INK'D headphones (just a little background info) When I first got my Droid, the headphone jacked worked great-- From the start though, I could tell that it was a little loose. Within a few months, my headphones would keep cutting in and out while listening to music-- this was remedied by lightly inserting the headphones, however it was not practical because the headphones would just come out on their own because they were so loose. I brought back my Droid to Best Buy (that geek squad protection is actually worth it), and they replaced it with no questions asked. So onto my second Droid, less than a month in, my headphone jack shorts up again. I checked the headset jack the moment I got my new Droid and it was much sturdier than the last-- I can deal with the fact that maybe I just got a bad unit the first time around. Now, what has happened is that whenever I bump my headphone connector, the phone thinks that they have been removed. The top part of the 3.5 pin, I believe is digging into the plastic headset connector on the Droid-- this in turn lets the headphones go deeper in than they should. It's almost impossible to keep my headphones correctly inserted-- they go in way to much and now the headset is loose again. To make a few things clear, to people who think I could possibly be negligent , I know not to keep my headphones plugged in and then to wrap it around the phone... I unplug my headphones all the time when I am done using and I make sure my Droid isn't cramped within my pocket. Coming from an iPhone, I actually did do the above mentioned things to the phone and it still withstood better than the Droid. I love Google, I love Android, but if this persists I may exchange for a new device. Any ideas? Questions/tips/need more info?