Just for the sake of future googlers. I’ve encountered the same problem (with 
horizon actually) and managed to solve it.

1) install and link latest openssl from homebrew: brew update && brew install 
openssl && brew link --force openssl
2) run tox, it fails.
3) manually activate the environment you want: . .tox/venv/bin/activate
4) build cryptography package with brew ssl: 
LDFLAGS=-L/usr/local/opt/openssl/lib CPPFLAGS=-I/usr/local/opt/openssl/include 
pip install --force-reinstall --upgrade --no-binary cryptography cryptography
5) deactivate

that’s it — that should do the trick. Someone might be able to suggest a better 
way to do this, but this variant works for me. (As long as I do not rebuild 
venv too often =))

-- 
Kirill Zaitsev
Murano team
Software Engineer
Mirantis, Inc
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