Steve Dower added the comment:

It's no less expected than having OS functions fail because the path is too 
long.

Using it to maintain dots at the end of directory/file names is a little less 
safe and may break some code. Maybe pathlib should strip these if there is no a 
prefix? (For example, "C:\Test." == "C:\Test" == "\\?\C:\Test" != 
"\\?\C:\Test.")

If most (or all) of the file handling functions in Python are using *W() APIs 
and can support the prefix, I'd rather add it in silently if only to avoid the 
long path issue. It's really the sort of implementation detail that pathlib 
should be able to hide from the app developer and the user (Node.js does this, 
for example, as its node_modules hierarchies regularly exceed the max path 
limitation).

Maybe the best approach is to preserve the prefix if it already exists, and add 
it if it becomes necessary. File operations are most likely to succeed in this 
case, even if it may be surprising to users.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue22299>
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