I support a number of laptop users. In the past (before there were many laptops), each user's computer was set up so that their My Documents folder was mapped to a shared folder on the server. This worked very well for desktops, but has several obvious downsides for laptops (no files when you're off-site, etc).

I'm exploring several alternatives for laptops to better map the shared drives, and SyncToy seems the best so far. I have a couple trial users set up so that it syncs automatically whenever they log in, along with a desktop icon they can click if they know they'll need something saved before the next login.

My problem is that I'm concerned how I, as the maintainer of this system, can spot failures. I don't want my first indication of a problem to come after a user drops their laptop in a lake and it turns out nothing was synced for the last year. Any ideas?