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 Continue reading...