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I’m sorry, but VSS is my choice for Worst App Ever. Let me enumerate some of the reasons:

1. It’s almost unusable over the Internet (specifically, over a VPN) even with these tips.
2. It regularly corrupts files! This is your Version Control System, not your mp3 collection! Corrupting files is like saying it’s OK if your Bank makes subtraction errors!
3. There’s no convenient way to see what’s not under version control, but still in the same tree.
4. It requires a GUI that is slow and often fails to respond. This is especially true over a network.
5. There’s no “server” setup. You have to use a shared drive to have any sort of “shared” repository.

But my number one problem with VSS is that it is totally unintuitive. I’ve used RCS, CVS and Subversion… so I’m no slouch when it comes to version control systems. It just doesn’t make any sense to me. Even simple things are confusing. More complex tasks like branching and merging get jumbled-up under names like “sharing” and “pinning”. Heck, even the MSDN docs say that merging is nearly impossible.

No doubt about it: Visual Source Safe is the worst app ever.