When we recently rolled out about 250 computers, three users had problems with their roaming profiles. Those users didn't find the last version of their profile on their new computer because their profile was not updated anymore on the server. Every year or so, I encounter the same problem with my own profile. Usually I don't realize that the synchronization failed because I got no error messages. We only backup user data from the file server. That's why this is really annoying since I only realize weeks after, that my data was not backed up anymore.
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The question is: What can you do if a roaming profile is not synchronized anymore with the server? That's where it can get really annoying. If you check the Microsoft knowledge base you will find many possible causes. You will find even more possible causes if you google for that problem.
A typical cause is a filename in the user profile which is longer than 260 characters. Often Web Links in a the favorite folder are the cause for this. Another problem could be that the user encrypted files with EFS. However, there are several other reasons.
Today, I found a new interesting case when my own profile wasn't saved anymore to the server. Somehow ntuser.dat which contains the user part of the registry had a problem. I was not able to rename it, even after rebooting and logging on with another administrator account. The file was still in use. Then I found out that Sophos antivirus caused the problem. One of its services was running under my own user account. I changed it to another account, et voilá, my user profile synchronized again with the server.
In my experience the easiest way to solve the problem with roaming profiles is to create a new profile and copy all the data from the old profile. Usually this is much faster than trying to find out what went wrong with the profile. Logon with an administrator account and rename the folder of the profile. Don't try this with the account of the owner's profile. You will only get an error message because ntuser.dat and ntuser.dat.log are in use. Don't forget renaming the folder on the file server, too. When you have a new profile, you can copy all files from My Documents to the new local profile. Maybe you also have to copy some desktop icons. Some applications might lose their user specific settings.
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If this is a serious problem for you or if you really are curious to find out what went wrong with your profile, you can check Usereven.log in c:\windows\debug\UserMode. Maybe you are lucky and can find some hints there. If you have problems with certain folders in your profile, you can try to exclude them from the synchronization process. All you have to do is adding them to user.ini in the root folder of the user profile.