gistfile1.txt

# force-link openssl
brew unlink openssl
brew link --force openssl

# set up a python environment with a non-Homebrew python.
# you can do this by installing pip against system python, or you
# can do it with a virtualenv.
pip install virtualenv # do this with any Python
virtualenv -p /usr/bin/python /tmp/systempython
source /tmp/systempython/bin/activate

# install cryptography with system Python
# no-use-wheel disables installing from the user cache of previously built wheels
pip install -U -v --force-reinstall --no-use-wheel cryptography pyopenssl

# will fail
python -c 'import OpenSSL'

# shows system OpenSSL link
otool -L /tmp/systempython/lib/python2.7/site-packages/cryptography/hazmat/bindings/_openssl.so

# clean up
deactivate
rm -rf /tmp/systempython