I have never been a great fan of the Winchester factory ammo for the .256 although the hollow point is quite explosive. I will never forget my father's reaction to an armadillo he saw me shoot over 35 years ago. We usually hunted them with .22 rifles, which worked fine, but that day I had brought along the Contender in .256; the armadillo fairly exploded, and to say Dad was impressed would be a gross understatement!
I load my .256 custom Contender carbine and my 10" barrels pretty warm and have not had very good case life with the Winchester brass. Formed cases from Remington brass seem to last longer for me, but I lose quite a few in forming. Basically, I've come to two solutions. First, I've changed the extractor to a .223 one as mentioned above, but I form cases from .221 Fireball as there is less trimming and the case necks aren't so thick as to need reaming. This brass lasts a L O N G time. In my Merrill pistol, which has a spring loaded extractor and requires a rimmed case, I use blown out .22 Jet brass, which forms to a bit of a short case, but the neck is long enough to hold the bullet. It works fine, lasts much better than the Winchester stuff, and you never have to trim it. :-D Yes, .22 Jet cases are hard to find, but I've amassed a supply that will last me until I die and leave plenty for whoever ends up with the Merrill. If you want to go this route, try Graf's; they sometimes have them.
Good luck with your .256 Win!
RonF