Tim Golden <m...@timgolden.me.uk> added the comment:

I think I've got down to the determining factor. For info:

PYTHONHOME has nothing to do with it: the same thing happens if I cd into 
PCBuild\win32 and run python_d.exe directly

For historical reasons the directory in which I'm building 
(c:\work-in-progress) is actually a junction to c:\users\<me>\work-in-progress. 
There is some commentary in the API docs about traversing junctions, so 
presumably that's special-cased in some way which results in an uppercase drive 
letter.

If I rebuild in, eg, c:\temp which is a normal directory, I don't see the 
uppercase conversion. So, while I still need to fix the underlying test to be 
case-insensitive, it looks like the Mystery of the Uppercase Drive Letter is at 
least mostly solved.

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Python tracker <rep...@bugs.python.org>
<https://bugs.python.org/issue34195>
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