I can't help with your particular problem, but I remember my own pains using SourceSafe just a few years ago.
If you have a choice on the source control system you use, I'd recommend taking a look at other options. There are several good ones to choose from.
I switched to SVN and never looked back. It is light-years better than SourceSafe and setup only takes a few minutes if you use visualsvn server (a free product). As for Visual Studio integration, visualsvn client is about $50, or just use ANKH + Tortoise (both are open source and very good). Bottom line is that the switch doesn't have to cost any money, and the installer packages are quick to get the system running on both the clients and the server.
Hope that helps, and good luck with SourceSafe if you have to keep using it.
Update: See also, this thread