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You need a touch more crimp.
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At least "a touch more."
OP, the gage shouldn't really interact with the bullet (your barrel is a different thing). The first step is to see if your loaded rounds are giving you problems because of belling/crimping. If not, THEN see if it's the bullet profile that's causing problems, using your barrel.
If you're not removing enough of the flare you applied before seating the bullet, the mouth of the case will be too big and will stop the round before it's all the way in. Just like in your chamber.
As meistermash noted earlier, a 9x19mm case is tapered.
The mouth of the case must not only stop the round on the chamber's headspace shoulder, it must be small enough in diameter to get to that shoulder.
This is less troublesome with jacketed bullets for two reasons. First, they're typically 0.355" in diameter while lead (and plated or coated) bullets are 0.356 (or more). Second, since lead bullets are also more easily deformed in seating, we tend to be a bit more "generous" when we bell cases.