The screw was too long for the insert. I had a nylon washer kicking around that I put under the screw head and once I did that, the strap tightened no problems. Unfortunately the washer was squished pretty easily and I don't have any more of them.

The washer size required is pretty odd. OD=13 mm, ID=7mm, and about 3mm thick. The closest I could get locally was still too big on the OD, but it works nonetheless.

I ended up 3D printing a set of washers with ABS. They fit well and I'll see how long they last.

For what it's worth, I've been removing/adding my back footstraps as I switch between foil and fin. I'm hoping to soon have a set position for them in the back and then I won't have to touch the straps again.