Relevant to various discussions of bits cutting deeper than expected, I was watching this amazing woodworker on YouTube accidentally ruin a very expensive project with his CNC machine (not a LongMill - but completely relevant): https://youtu.be/j34KtFaFyQs?si=Z4PrMqcM_3E6tENU&t=1840
The video is timestamped to the exact moment of his big “oops” - where he had an upcut bit pull itself too deep into his workpiece, ruining an expensive walnut slab, and thus his entire piece.
I have in the past theorized that upcut bits can pull themselves into the work (and I have confirmed it when I have had bits clearly pull themselves out of my collets). This video shows the consequences.
Short version - make sure your bits are always tight, and downcut (if it is suitable) won’t pull itself into your workpiece.