Hello. We have a 2008 R2 Standard server running Remote Desktop Services allow users access via our VPN Portal. We are using roaming profiles with redirected desktops and My Documents. The issue is some users lose the contents of their My Documents on login. It appears to happen when the Applying Redirected Folders takes place during login. It is like the policy is trying to access the data but for some reason can't so it deletes the folder and creates a new one. The difficult part of this issue is other users can login fine with no issues and can do it consistently. Most that are experiencing this problem experience it at random so when we in the IT department login as the user (after restoring their data from backup) it works fine. Only one user so far experiences his Documents folder being deleted everytime (and he has become our guinea pig).
So our setup is Desktop, Appdata and My Documents are redirected to the users home folder via Group Policy. I have confirmed that permissions on the folders is correct and the system does have access to it.
It gets weirder still though because I built a completely new server on VMWare (Old one being a physical server) and transferred our RD CALs over to it. It does the exact same thing. Nothing was transferred from the old server as this was built from scratch and is completely up to date. I have also tested the account of the one user who fails everytime and found if I delete his roaming profile and then log into the server it works. But as soon as I log him into any other computer and then try the server again it fails. I can't find anything in the profile that would cause this issue. I didn't even use that users specific computer, I used another one that is a fresh build.
So any suggestions would be really appreciated. Let me know if anything needs to be clarified. Thank you.