Greetings @Jhon,
The 44 WCF (later .44-40) is a very old cartridge and the chambers can be all over the place. I would be reasonably sure that your problem is an oversize section on the case where the die can not reach. This happens with belted cases as well. As mentioned above size the case with the case sitting on top of the shell holder and drive the case out with a rod. You may have only have to do this once. Definitely do NOT grind the shell holder, it will likely wreck it. You should consider keeping the cases separate for the two firearms and a different head stamp would help with this. Lastly they are 44 WCF and not 44 mag and the cases are thin so I suggest keeping your loads down to the lighter end of the data. Your brass will last longer.
Regards Grandpamac.
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