Originally Posted by
bonsai171
Wow, my bad. Now that I think about it, there aren't any cutouts in the steerer. That doesn't make any sense

Makes perfect sense. Cutting holes in something meant to take an internal expander seems rather risky.
Originally Posted by
bonsai171
Is it possible the steerer tube is slightly tapered? Not as much as a Bombtrack frame, but enough to throw off the threaded adapter?
The steerer began as a tube.
It might be widened in spots, by enthusiastic tightening of previous quill stem wedges.
But an accidental taper - not very likely.
Maybe the ID is overall a little wide, and maybe the OD of the adapter is overall a little narrow.
I'd still start by Another look at the headset, a far more common cause for play in this area.