Occasionally, the Windows 7 workstation is just not trying to load the roaming profile, leaving the user with his or her (outdated) existing local profile.
There are no errors or warnings in the Windows Event Logs; the only thing I have noticed is that in the User Profile Service Operational log, there are no log entries (Event IDs 6 and 7, source User Profile Service) indicating any attempt to synchronise the user profile from the server at that login.
Read this link: msmvps.com/blogs/bradley/archive/2009/02/21/… and there is a link to the Microsoft document regarding how this works (It is for Vista, but the same for Windows 7).
There are several ways to achieve what you want - one clunkier than the other.
Terminal servers can be a deployment nightmare - users may not have rights to run and hence MSI self-repair could fail.
So far it has affected one user three times and another user once that we know of.
The machines in question are VMware View virtual machines, and there are no abnormalities on the VMware View side of things either.