In case anyone else bangs their head against this – in SourceSafe, there seems to be a bug in recursive file handling using the command line tools. I tried performing a recursive checkout using a specific filename (AssemblyInfo.cs, in this case), but SourceSafe claimed to not find any matching files. However, if I specify a wildcard character (AssemblyInfo*.cs), it works as expected (although it wouldn’t be exactly the right behavior if I had an AssemblyInfo2.cs file). In other words, this:
ss checkout -R AssemblyInfo.cs
does not work, but this:
ss checkout -R AssemblyInfo*.cs
does.
It appears that the recursive behavior requires a wildcard character to work correctly.