Had system update, company added Symantec WSS to OS. But caused issues in VM since didn't have cert.
Found cert near WSS executable and added to VM. Added to some apps, but had issues with pip and pipenv.
Solution was to fix pip with:
pip config set global.cert /path/to/wss-ssl-intercept-ca.crt
Then to fix pipenv with:
echo 'export REQUESTS_CA_BUNDLE=/path/to/wss-ssl-intercept-ca.crt' >> ~/.bashrc # or .zshrc, in my case