Greetings Micky,
The Winchester necks are much thinner so only the Redding die sizes them enough to even touch the expander ball. It is just a matter as selecting the die that is the most appropriate. I tried to neck size my .30-40 Krag brass with a .308 Win neck die but it did not size enough and needed to partial size with the Krag FL size die. It is all good fun finding the solutions. The more you learn about handloading the more complicated it seems to become. Some cartridges are easy but others not so much.
Regards Grandpamac.
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