Following up, here. I figured out the solution was corruption of my fresh windows VM. The following solution resolved my issue:
To make things more complicated, it broke on my next try at authenticating. Through more troubleshooting, I discovered that IE 11 was breaking this functionality. The site I'm authenticating agains must not have good IE 11 functionality. After trying the fix again, and using Edge instead of IE, I was able to authenticate several times without it breaking
Thank you, @Carl Fan for your initial reply!