This article details some of the hoops I had to jump through before I could authorize my Let’s Encrypt cert via Certbot, hope it helps the next guy.

Compatibility

Certbot used to only support python 2.7 and above, but recently began supporting again. That’s good news as CentOS is still on Python 2.6.

Danger: CentOS requires the particular python version it comes with, so do not attempt to upgrade 2.6 to 2.7!

There are some guides on how to install python 2.7 side by side 2.6, but as of the time of writing, it is unnecessary to do so. Certbot can detect if python 2.6 is used and support it accordingly. If you did install python 2.7 as well, it may confuse the auto-detect script in certbot and cause it to attempt to install unneeded packages which will lead to conflicts.  Read More