This also affects the -m ensurepip installation of pip itself: the pip install fails trying to upgrade the Apple-supplied version of setuptools. The behavior of adding the system Python's site-packages directory to the search path of all framework-build Pythons was deliberately added as a result of Issue4865. I think experience has shown this was not a good idea because of the coupling it introduced between separate Python installations and some third-party distributors of Python on OS X already patch this code out. It's currently only an issue for 2.7.x since Apple has not yet shipped versions of Python 3.x but the code should be removed there, too.