Even if you trimmed first, and then size, the cartridges would still fit in the gauge. If you trimmed to max length (and who does that?), the case mouth would only be long by a few thousandths.
There are at least three reasons the entire rim of a case will stick out of a case gauge. Two are fairly common. The case is a little too fat, or there's a ding on the rim.
A case that's slightly too fat can cause your rifle to fail to go into battery. But by the time it does that, the rounds are going to seize in there the way an unlubed case will seize up in a sizing die.
There's a third reason the entire rim of a case/round will stick out of a case gauge. It's because the case is simply way too long from shoulder to base. And these cases can fail to size until you anneal the shoulders.
Case stretching (and resulting shoulder separations) seem to be a lesser known problem that can be caused by semi-auto rifles. This is the only discussion I have found about it. And the reason it's so little known is probably covered in response #34
"30+ years ago I was building/tuning AR rifles to better suit the rounds being fired through them,
and to this day eyes glaze over instantly when you start the conversation about gas pulse pressure AND duration..."
https://thefiringline.com/forums/sho...=575254&page=2
Perhaps OP has an offending rifle, or he got his brass from one.