For starters, when was the last time you replaced the contact tip? They are considered a consumable part and must be replaced regularly for optimum performance.
Secondly (and more likely), when was the last time you either cleaned or replaced the cable liner? After awhile, they build up enough crap in there that the wire starts to really drag. Often, a bunch of the crap in there will work it's way down the liner and clog the tip, causing the wire to jam.
While you're in there, make sure the drive roller clamping pressure is appropriate, and the spool tensioner is not too tight.