Glad this thread was resurrected! I have a Speck Fitted case and just wanted to let you all know that the Westone plug DOES NOT fit. I really love this case and don't care to just have a "snap" case without any protection on the top and bottom, so I went to Radio Shack and got an 8" volume extension. Not the best solution, but for $8, it'll do for now.
Another dilemma is the dock connector. My connector coming from my DICE interface in the car is too big for the case also. It seems to be hollow-ish sounding plastic on the base to just try to Dremmel it down slimmer so I'm stuck as to what to do there also. Buy an adaptor that's slimmer/smaller?? Buy a nice ProClip holder with passthrough?? All this to keep a free case that I really love for my phone!
Any advice on the dock connector issue?