DougK,
You can do the same thing Skeettx mentioned by putting any flat piece of steel on top of the shell holder to push the case all the way up to the rim, into the die. You can do this to see if that is the problem, then decide what to do about the shell holder. A thinned shell holder and stuck case=busted shell holder. BTY, if you try either suggestion, remove the expander so you can drive a stuck case out. I use a "pusher" I made up with a flat top and the bottom like a shell holder, it works for everything ( but I have to drive all cases out). On reflection and going back to your first post, I wonder if using a 250gr bullet in a chamber cut for a 200 or 193 gr bullet is the cause of your problem. I suggest you smoke the bullet of one of your handloads and chamber it. When you extract the cartridge, check the bullet for bright marks caused by the lands in the barrel.
Mike