I am on a Mac running Yosemite (Mac OS X 10.10.1) and homebrew installed python and python3 and python -m ensurepip --upgrade does not seem to be working as I w
Per the documentation:
This module does not access the internet. All of the components needed to bootstrap
pipare included as internal parts of the package.
and (emphasis mine):
To ensure the installed version of
pipis at least as recent as the one bundled withensurepip, pass the--upgradeoption