Hey Mike,
One more update before I head out for the day. I went ahead and deleted all users that were created via the import and reseeded the users table ID. I'm seeing varying results now with my testing.
I first logged in to my machine as user A, browsed to the site, and viola - it worked! - logged me in just fine.
I then logged in as user B, browsed to the site, but did not get logged in. No errors & nothing in the event log indicating that any attempt was made to authenticate against AD.
I then followed the Login link and logged in manually - worked fine - authenticated against AD and created the user.
I then deleted both users again and ran the test again. This time neither user was logged in/authenticated against AD automatically, but again, when I logged in manually it did authenticate and create the users.
Do you know why it doesn’t always authenticate against AD went the user browse to the site?