The problem ended up being that the shell wasnt entering the die completely. Like CatShooter explained about how a press "flex's". Even though a die can be set up correctly (The base of the die touching the shell holder) when a shell is inserted into the die the press "flex's" and doesn't allow the shell to enter fully. So I took his advise and turned the die down another 1/4 turn to adjust for the press "flex". I also took a little advise from Jabey9210 and shimmed the shell holder so that the casing was as far "up" in the shell holder as possible. These 2 things combined allowed enough of the shell to be resized that I can now chamber them in my rifle.