Mine is the same as yours, hard to put in and hard to pull out at that deepest part.Ok last night I tried again with the same headphones, and I was able to get it to click in all the way. It is a hard click though, definitely doesn't feel like the normal fit.
So now I know that it works, but not well. Should I try taking it back? Does anyone else's XL headphone port work fine? As in not requiring crazy pressure to get the plug in?
Personally I'm not going to worry about it, it's not like a defect or something where it'll explode the next time I need to apply pressure, and the sound is fine too.