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I'm using Sierra 300 grn hollow points. I'm crimping on the cannelure, but then when I pull the bullet the mouth of the brass didn't leave a groove, or cut, in the cannelure. Should it?

No,you don't want the crimp to deform or cut the bullet/groove or cannelure in any way. It just needs to be tight enough to hold the bullet securely under recoil. If you're crimping into a groove/cannelure,it doesn't take a real heavy crimp. I crimp just tightly enough that looking at the nose of the bullet,I can't see any of the rim of the case in the cannelure. A good easy test is to push the seated crimped bullet against your bathroom scale. If the bullet doesn't move at 60 lbs of pressure you should be good to go. Load your magazine and as you fire each round,unload and measure case overall length with your calipers if you want to be certain the bullets aren't setting back,though its pretty eay to tell by looking at any exposed cannelure. I go with a little heavier crimp than necessary to get a little better powder ignition.
And get a Lee Factory crimp die,its the only way to go. And cheap!
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Jeff

I'm NOT the JScottRupp of Wolfe Publishing.