Hopefully if anybody runs across this - this will help. The issue is that STW creates an actual user. I know that kind of goes without saying - but in my case I was logging in and out as admin
as well to administer some other things on my box.
Because of that it wasn't caching the logged in user as my AD user. When I logged in with my AD user name and password through the login screen it leveraged the AD authentication and logged me in as expected. But I did in fact have to login manually.