Through the past three years, despite me not updating this blog, I did keep updating the site's certificate just to keep it running. A couple months back I suffered a hard drive failure, and now that the certificate is expiring again I was faced with the prospect of re-installing certbot.

For me, at least, certbot/letsencrypt has been a constant battle. Every 3 months I need to remember the arcane sequence of commands, which virtualenvs I had things installed in, and the like. But for the most part a series of scripts kept it manageable. But reinstalling certbot, along with the plugin I needed to use, was another ordeal entirely.

The first issue was that certbot is currently designed to run on the same web-server that it is providing certificates for, which is not an option with a site hosted on an S3 bucket like mine. The alternative was a tool called 'certbot-auto' available here that behaved... kind-of like the old certbot. Finding out how to install it (3 options, the link above, with apt, or with pip) took a fair bit of experimenting, and then where to install it (virtualenv) took a fair bit more; and that goes double for the plugin 'certbot-s3front' mentioned in my first blog post.

At the end, it turns out the linked utility should be run directly, and the plugin then needs to be installed in a special virtualenv located in /opt/, owned by root. So I needed to first run the following

sudo -i
source /opt/
pip install certbot-s3front

And only then did things work as described in my first post.

Well... nearly. It turns out that in addition to doing things in a special virtualenv certbot-auto also does things with a "fresh" set of environment variables, so passing the AWS credentials via environment no-longer works. After fighting this too for a while I realized there was no simple solution, the plugin itself would need a new version to address this issue.

So I made a new version.

And with that installed things finally worked... until N eed to update the certs again.

I also made a pull request to get merged it into the main repository, I don't fully know if it's necessary because I don't know if everything I did here is wrong anyways. Right now it's held up because it's failed on a Microsoft... thing, and also needs the approval of the maintainer of-course, but if that gets merged I'll update the article. Until then, here's to another 3 years!