The once fired stuff was already fire formed to fit the .308 chamber it was fired in. When you full length size, your die might be set so that you are not bumping shoulder at all. This wouldn't matter on the new brass, and you wouldn't notice any problem, as it's likely already at spec. The once fired stuff though may have a wee bit higher shoulder...just enough so it won't chamber, or will only do so with more than normal force. You could try adjusting the die downward a very little bit at a time and see if you reach a point where the brass chambers easily...course if you start to buckle the brass before you get a fit, you'll definitely know that's not it! Also, if you set the shoulder back too far, there's a chance you'll start to get either get head separations, or at least see signs of stretching brass just above the head...a mistake I made with some 7mm R mag a while back. To see if you are/are not hitting the shoulder, you can blacken the outside of the neck and shoulder with something like a Bic permanent marker, then run it through the die. It will be obvious from the markings on the blackened area where the die touched and where it didn't. Once it's been fired in your .338, you can used the same Bic marker method to set your die so that you are just neck sizing...as long as you keep it trimmed, it will fit your chamber perfectly, and you will maximize the life of your brass. I make all of my .358W from .308 brass...no grief so far. Apologies for being so long winded, especially if you already knew this.