Why not save them for 9mm and get the right bullets?
For ANY roll crimp job, get a Redding Profile Crimp Die.
You can roll into the plating, but you can also cut through the plating and have problems.
One trick that has been done for over 100 years is to seat the bullet deep enough that you can just roll crimp over the bullet ogive. Round will look slightly weird, but they won't back out of the case and lock up a cylinder.
Otherwise, simply taper crimp them and check the last two rounds in each cylinder full to see if the bullets are creeping out of the case.
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