Anyone ever have a freeze plug pop out??

The "shallow", "thick" plugs can pop out if they're not square in the bore.
I don't like those plugs.
The deep thin plugs are much less likely to do that.

I don't use any sealant on brass plugs normally.
If I felt the need, I'd use something like copper coat.

I've used an appropriately sized socket for over 30 years.