Steve Dower added the comment:

Arguably it isn't even against the documented behavior, since a component 
starting with a slash an absolute path.

I'd be in favor of preserving the drive when encountering a component starting 
with a separator. Not sure of the value in changing the behavior in older 
versions - apparently I've never encountered this before, and I feel like I 
should have.

----------
resolution: not a bug -> 
stage: resolved -> test needed
type:  -> behavior
versions: +Python 3.7 -Python 2.7, Python 3.6

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue30906>
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