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In looking at another os.path.join documentation issue I tried the Windows join to see if it matched the docs, and found that it was very unclear. I searched the tracker and found Issue 1669539, which contains much relevant discussion but also much discussion of possible enhancements. So I'm opening a new issue *just* about what I see as the current bugs in the os.path.join docs and ntpath.join implementation.
I'm not qualified to fix this, not being a Windows user, but it is clear to me that the documentation of os.path.join for Windows is unclear (it does not indicate what is considered an absolute path on Windows) and wrong (\foo will *not* restart the path if it is the second element and follows a drive specification, but it does any other time), and that the current behavior may have a bug if, as seems to be implied by the issue 1669539 discussion, something that looks like a drive specification in the middle of a path is invalid on Windows. If this last is not a bug, it should be mentioned in the documentation, since the actual behavior is counter-intuitive.