Martin Panter added the comment:

I don’t have much to do with Windows, but I understand we don’t support 
surrogate-escaped bytes there. E.g. see 
<https://docs.python.org/dev/library/os.html#os.fsdecode> and 
sys.getfilesystemencoding(). However I suspect your first patch would have 
failed on Windows doing os.fsencode(TESTFN_UNENCODABLE); apparently it cannot 
represent all possible file names in bytes. The second patch doesn’t call 
fsencode() so this shouldn’t be a problem.

Your tests do not test that the output is valid Unicode without surrogates. 
With your first patch applied, when pydoc wrote the HTML to a UTF-8 disk file, 
I got the error:

  File "/media/disk/home/proj/python/cpy\udcffthon/Lib/pydoc.py", line 2626, in 
cli
    writedoc(arg)
  File "/media/disk/home/proj/python/cpy\udcffthon/Lib/pydoc.py", line 1659, in 
writedoc
    file.write(page)
UnicodeEncodeError: 'utf-8' codec can't encode character '\udcff' in position 
674: surrogates not allowed

I have been working on an alternative patch using my IRI (Unicode URLs) 
proposal for “file:” links, and “surrogatepass” for HTTP links. But I am also 
trying to fix some related problems with the built-in HTTP server, and the unit 
tests are a bit tricky.

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue25184>
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