How about when the good tools are free (as far as money), but your boss doesn't want to use them because that would require him (as well as co-workers) to learn something new?

My current employer still uses CVS. No one really uses it properly. I see output files committed to repositories and I think I'm the only one who writes commit messages since I haven't seen anyone else's when I look through the history. I haven't seen anyone else create a branch.

I've mentioned Git both in private and in group meetings, but it always falls on deaf ears. So I use Git via Cygwin and always keep it local on my machine. I have Git ignoring the CVS directories and CVS ignoring the .git directory. The master branch is for things that I check-in to/update from CVS. All my real work is done in Git feature branches.