Correct. I just logged into my portal this morning and, believe it or not, it took me out of the AD role that I added myself to the other day! I'm back to square one. In my testing, the role sync would seem to work immediately after logging in. I would create a same named group from AD in DNN roles that my test user was in, logout and login as my test user and the role was updated with his name. Logout and back in a couple of times to make sure it "stuck" and it was working. Then, I would even remove the test user from the role, logout and log back in as the test user and he would get put back in the role. Perfect. Now, however, it isn't happening. I added a role name just like from AD (I use the pre-windows 2000 name) and logout and back in, but it's not being put into that role. I verified my authentication settings, user and password, still no good. Now, I manually add myself to the role, logout and back in, and it takes my name out of the role! Ouch. Sorry to be the bearer of bad news.
On the plus side...it did not take me out of the existing roles, AD groups or DNN groups. I'm going to try another test...the role I added was at the bottom of my membership list in AD. I'm going to create a role that is found higher up in the list to see if that gets updated. If it does, then it could just be that it isn't getting all the way through the membership list....
Hold the phone! ! ! ! In my haste to test this I just realized that the group I added wasn't a security group, but a distribution group. Duh. I added a security group (a global group name) and it worked immediately. I want to see if global or universal makes a difference. Also, the group I had in there the other day that users were not getting added to was definitely a security group, so now I'm not sure if I have it working or not. Today should prove to be a good test. I'll keep you posted.