Re:Python 3 Is Winning Library Developer Support
by tclancy on Wednesday March 09, 2016 @06:16AM
(#11252247)
AFAIK (and I have dozens of virtualenvs running on a Windows box) you can upgrade pip, it's just one of a handful of packages that throws an error at the end because it was unable to delete the folder it created during the install process. The upgrade works, it just looks like it doesn't. But maybe that's only true inside a virtualenv.
If it is not, you can often do python -mpip install xxxxx
And you're right there are some gotchas - for instance pip install -U pip won't work to update pip itself as on Windows a program can't seem to overwrite it's own executable.