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Edit Admin
If the IOError.Exists exception corresponds under the covers to the POSIX "EEXISTS" error value, you only know that something with that name exists. The "something" might be a directory, but it just as easily be a bound UNIX socket, a terminal character device node, a symbolic link, or even a file. Good luck dealing with that.
The Windows documentation isn't clear, but could easily be trying to say something similar.
Edit Admin
Also, I wouldn't bother with all the "crawl back up to find where it first doesn't exist" junk. Just start at the shortest length and work toward the full path.