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/openssl points to ../opt/openssl/include/openssl. Does anyone know how to fix this? This started happening after I reinstalled python using brew install.

pip is configured with locations that require TLS/SSL, however the ssl module in Python is not available. Collecting Pillow Could not fetch URL https://pypi.python.org/simple/pillow/: There was a problem confirming the ssl certificate: Can't connect to HTTPS URL because the SSL module is not available. - skipping Could not find a version that satisfies the requirement Pillow (from versions: ) No matching distribution found for Pillow

UPDATE: Here's some more info:

✗ which python /usr/local/opt/python/libexec/bin/python 

✗ which pip /usr/local/opt/python/libexec/bin/pip 

✗ python --version Python 3.7.4 

✗ pip --version pip 19.1.1 from /usr/local/lib/python3.7/site-packages/pip (python 3.7) 

✗ brew info python python: stable 3.7.4 (bottled), HEAD Interpreted, interactive, object-oriented programming language https://www.python.org/ /usr/local/Cellar/python/3.6.5_1 (4,795 files, 100.0MB)   Poured from bottle on 2019-10-08 at 14:39:37 /usr/local/Cellar/python/3.7.4_1 (3,903 files, 60.6MB) *   Poured from bottle on 2019-10-08 at 14:37:10 From: https://github.com/Homebrew/homebrew-core/blob/master/Formula/python.rb 

Yes, I have both 3.6.5_1 and 3.7.4_1 installed as I may need to switch between the two at times.

✗ brew unlink openssl Unlinking /usr/local/Cellar/openssl/1.0.2s... 0 symlinks removed 

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.

---

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.

Answer 2

Mac OSX Catalina (and same issue on OSX Mojave) Pyenv

For anyone searching this topic, I had the same presenting problem, but had Python installed via both Homebrew and Pyenv!! It would have been better (IMO) to just use Pyenv to easily manage versions. As mentioned by @ivan_pozdeev in their answer, but here's some detail you might want.

If your situation is similar, none of the above solutions would be quite enough to set things right. Partially I was helped by a Pyenv related answer here: https://stackoverflow.com/a/51797298/3084820 I also happened to have pyenv-virtualenv installed, so mentioning that as well, as it's common to use these two together.

I finally took the following steps to resolve the issue:

brew uninstall python rm -rf $(pyenv root) brew uninstall pyenv-virtualenv   # you may not have this installed, but... brew uninstall pyenv 

Now, for a clean installation manageable with Pyenv:

brew install pyenv pyenv install 3.6.10  (or whatever version you want) 

This gave me a clean, working install of Python 3.6.10, and if I wanted or needed to, I could install a different version and switch between with Pyenv.