Virtualenv fails on OS X Yosemite with OSError

Question

I recently updated to OSX Yosemite, and now I can't use virtualenv / pip.

Whenever I execute:

virtualenv env

It throws a:

OSError: Command /Users/administrator...ux/env/bin/python2.7 -c "import sys, pip; sys...d\"] + sys.argv[1:]))" setuptools pip failed with error code 1

And within that stack trace pip throws:

ImportError: cannot import name HTTPSHandle

Has anyone else encountered this error? These questions suggest updating homebrew to solve the issue. Which I've done but the issue still persists.

• ImportError: cannot import name HTTPSHandler using PIP
• ImportError: cannot import name HTTPSHandler installing get-pip.py
• ImportError: cannot import name HTTPSHandler using Brew

Full Stack Trace:

Administrators-MacBook-Air :: ~/dev/KaggleAux ‹master› » virtualenv env                                                                                                                               127 ↵
New python executable in env/bin/python2.7
Also creating executable in env/bin/python
Installing setuptools, pip...
  Complete output from command /Users/administrator...ux/env/bin/python2.7 -c "import sys, pip; sys...d\"] + sys.argv[1:]))" setuptools pip:
  Traceback (most recent call last):
  File "<string>", line 1, in <module>
  File "/usr/local/lib/python2.7/site-packages/virtualenv_support/pip-1.5.6-py2.py3-none-any.whl/pip/__init__.py", line 10, in <module>
  File "/usr/local/lib/python2.7/site-packages/virtualenv_support/pip-1.5.6-py2.py3-none-any.whl/pip/util.py", line 18, in <module>
  File "/usr/local/lib/python2.7/site-packages/virtualenv_support/pip-1.5.6-py2.py3-none-any.whl/pip/_vendor/distlib/version.py", line 14, in <module>
  File "/usr/local/lib/python2.7/site-packages/virtualenv_support/pip-1.5.6-py2.py3-none-any.whl/pip/_vendor/distlib/compat.py", line 31, in <module>
ImportError: cannot import name HTTPSHandler
----------------------------------------
...Installing setuptools, pip...done.
Traceback (most recent call last):
  File "/usr/local/bin/virtualenv", line 11, in <module>
    sys.exit(main())
  File "/usr/local/lib/python2.7/site-packages/virtualenv.py", line 824, in main
    symlink=options.symlink)
  File "/usr/local/lib/python2.7/site-packages/virtualenv.py", line 992, in create_environment
    install_wheel(to_install, py_executable, search_dirs)
  File "/usr/local/lib/python2.7/site-packages/virtualenv.py", line 960, in install_wheel
    'PIP_NO_INDEX': '1'
  File "/usr/local/lib/python2.7/site-packages/virtualenv.py", line 902, in call_subprocess
    % (cmd_desc, proc.returncode))
OSError: Command /Users/administrator...ux/env/bin/python2.7 -c "import sys, pip; sys...d\"] + sys.argv[1:]))" setuptools pip failed with error code 1

Answer 1

Solved with:

brew uninstall python

brew install python 

pip install --upgrade pip

*Note: You'll also need to a do a fresh pip install for any current projects you're working on.