Paul Moore <p.f.mo...@gmail.com> added the comment:

On Sun, 17 Feb 2019 at 14:12, jt <rep...@bugs.python.org> wrote:
> subprocess.CalledProcessError: Command 
> '['C:\\myproject\\tools\\windows\\.python-win\\spen-venv\\Scripts\\pip', 
> 'install', '--upgrade', 'pip']' returned non-zero exit status 1.
> C:\myproject>
>
> I would expect that to work even without --user so I'm not sure what is going 
> on

That's normal behaviour. You can't upgrade pip in-place with the
wrapper, the correct command is

    python -m pip install --upgrade pip

Paul

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<https://bugs.python.org/issue36010>
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