First up, we need to make sure that Skype is running its latest version. This can not only eliminate the bug which might have been causing the in the first place but ...

On a user's machine that I support as of today he cannot synchronize his offline files. We have the My Documents folder redirected to a server location ...

Well, I've wasted an entire Saturday on this on. Why the fuck Microsoft's system imaging tool is so fucking picky, I have no idea, but now I'm at a loss. I made an image using the System Image tool ...