Looks like a bug to me.
EDIT: This is really weird. I set up a test pocket and saw the same thing as you.
I then tried with the Advanced V-Carve and it worked, as expected.
Weird part: I went back to the pocket toolpaths and it worked without issue. About to test this again.
EDIT #2: OK, this had nothing to do with advanced V-carve, but there’s a repeatable issue with the start depth in a pocket toolpath.
@Dillon Change your pocket to a profile, then back to a pocket.
