Steve Dower added the comment:

Just discovered that this actually requires enabling the group policy for long 
paths - specifically setting 
HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\FileSystem@LongPathsEnabled 
to 1.

Apparently the manifest is also required, but in my testing the manifest is 
ignored and we just get long path support for free. So perhaps we should just 
add a message to file exceptions when the path is >260?

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue27731>
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