Visual Source Safe.   I cringe whenever a client site is using it.  Let's face it, when VSS 6.0 came out it was an acceptable product for its time (what was that.. 6 years ago? 7?).  It was pretty good for VB6 developers working alone or in small teams.   But VS.NET isn't  VB6.  The methodologies of development are different... unfortunately VSS treats them as the same.

One of the things I hate most about VSS is actually issues with VS.NET's SCC integration -- the crud that VS.NET puts inside project and solution files when using source control.  (Unfortunately, VSS's standalone client does the same thing for .net projects. Grr...)  What if you take a zip of someone's “working directory” home (where the VSS server isn't available)... ever tried to open a solution that way?  Not fun.

Luckily, Dave Bettin has just put up a tool he's had for some time now - NukeSourceSafe.  Go check it out.  It's useful even - no, especially - for those of you still using VSS.