You sure it is not the shoulder?
I have an issue with some mill brass where it doesn't want to chamber when it is first formed because the shoulder is more of a radius than a steep shoulder.
It doesn't matter if you undersize or oversize with your FL dies as the radius will still stop it from chambering.
At one point I oversized so much that the extractor was slipping off and it still wouldn't chamber right.
I can now get most to chamber the first time and fire so the shoulder is created.
I don't have issues after that.
Both tp555 and Marty from Teppu Jutsu have mentioned this to me or posted about it here.
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