Eryk Sun <eryk...@gmail.com> added the comment:

Geoff, we probably need a new issue for this, but first, please report the 
value of len(os.getcwd()) in a case where check_output() fails. 

Prior to Windows 10, the working directory is limited to MAX_PATH - 2 (258) 
characters. (Windows uses the last two characters internally for a trailing 
backslash and a terminating null.) However, even with long-path support enabled 
in Windows 10, CreateProcessW retains the original WINAPI limit, which I assume 
is because the current implementation doesn't know whether the child supports 
long paths. If the inherited current directory exceeds this limit, 
CreateProcessW fails with ERROR_INVALID_PARAMETER (87).

----------
nosy: +eryksun

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<https://bugs.python.org/issue35678>
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