SSL module in Python is not available (on OSX)

Question

I\'m having trouble running pip install in a virtualenv on OSX 10.13. I already have run brew install openssl and the path /usr/local/include

Answer 1

The ssl module as well as its underlying C extension appears to be a part of the python formula:

Mac-Admin:~ admin$ python3
Python 3.7.4 (default, Sep  7 2019, 18:27:02) 
[Clang 10.0.1 (clang-1001.0.46.4)] on darwin
Type "help", "copyright", "credits" or "license" for more information.
>>> import ssl
>>> ssl
<module 'ssl' from '/usr/local/Cellar/python/3.7.4_1/Frameworks/Python.framework/Versions/3.7/lib/python3.7/ssl.py'>
>>> import _ssl
>>> _ssl
<module '_ssl' from '/usr/local/Cellar/python/3.7.4_1/Frameworks/Python.framework/Versions/3.7/lib/python3.7/lib-dynload/_ssl.cpython-37m-darwin.so'>

so it being missing most probably means package installation corruption which brew reinstall python should fix.

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Also note that while Homebrew allows multiple versions to coexist, its installation logic isn't quite designed to keep the alternative versions operational unless they are installed via a versioned formula (and e.g. routinely removes old versions in the regular brew cleanup).

So consider using pyenv (also available via brew) if you need to routinely switch between Python versions -- or some 3rd-party tap that offers versioned formulae for it.