Glad it worked out.
Looks like it was adjusted for way too much crimp. You crumpled the case between the bullet and the carbide ring as mentioned earlier. The crimp ring may have been in upside down. Look at the crimp sleeve before you return it to the die. The end shouldn't push straight down on the mouth of the case. It should have a taper on the ID that rolls the mouth into the bullet.
Does the bullet have a cannelure? If not, I wouldn't try to roll crimp into it anyway.
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