A '*' in fnmatch.translate is converted into '.*', which will greedily match directory separators. This doesn't match shell behavior, which is that * will only match file names: decibel@decina:[14:07]~$ls ~/tmp/*/1|head ls: /Users/decibel/tmp/*/1: No such file or directory decibel@decina:[14:07]~$ls ~/tmp/d*/base/1|head 112 From a posix standpoint, this would easily be fixed by using '[^/]*' instead of '.*'. I'm not sure how to make this work cross-platform though. It's worth noting that some programs (rsync, git) support **, which would correctly translate to '.*'.