There's a unique challenge with seating lubed cast boolits into this bottleneck case: the neck tension is so low that it cannot overcome the pressure that is developed inside the case when you seat the boolit. It's literally a piston. I confirmed this when I held a case and seated boolit in the jaws of my calipers. I could pinch the jaws together with very little force and seated the boolit deeper, and then the boolit would rise up out of the case as soon as I released the calipers. Up & down, up & down - just like a piston. The grease helps to keep the air sealed and reduces friction in the neck. I've seen this with the Lyman 9mm Devastator and the RCBS 9mm-147-FN (with two grease grooves, which makes it worse). Grease grooves inside the tiny neck just further reduce neck tension.
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I was using AA#7 with the Devastator and I would just work the boolit until the air could escape. Now I'm doing a compressed charge of Enforcer with the RCBS, so I can't just work the air out. So, I decided to do a half crimp & seat simultaneously. Know that I generally hate seating & crimping in one step. I have some cartridges that I seat in two steps, and crimp in a third step (which is outside of the scope of this post). The first crimp is just barely enough to keep the boolit from acting like a piston; in fact, I can still easily push the boolit deeper into the case by hand.
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Then, I wait a day to see if the overall cartridge length grows. Confirming the length hasn't changed, I then do the second crimp using the Lee collet style FCD.
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I want to point out that you have to be very careful to not over-crimp the .357 Sig cartridge. Over-crimping will cause the tiny neck to flare out, and you lose neck tension. I once over-crimped a plated bullet that would spin in the case. I could not push in or pull out the bullet by hand, but it would easily spin in place. This cartridge has to be crimped just right.
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Also, seating & crimping simultaneously violates the guidelines in Lyman's 49th reloading manual. This process I described should not be done without previous experience and caution.