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
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.