Python Requests – How to use system ca-certificates (debian/ubuntu)?

I’ve installed a self-signed root ca cert into debian’s /usr/share/ca-certificates/local and installed them with sudo dpkg-reconfigure ca-certificates. At this point true | gnutls-cli mysite.local is happy, and true | openssl s_client -connect mysite.local:443 is happy, but python2 and python3 requests module insists it is not happy with the cert.

Can I resize the root partition without uninstalling and reinstalling Linux (or losing data)?

I have started using a machine that has both Debian and Windows 7 installed. However, after installing some programs I started getting a message that there is not enough space. I knew that the system had more than 1TB of hard disk space in total and did some research. It seems that the root partition is only 5GB.