HTTPS: What a terrible experience

Digital Ocean droplet with Docker all the things

Specifically all apps running in Docker containers, served on subdomains through the nginx reverse proxy container.

tl;dr I didn't figure it out yet, if you're looking for a guide you're not in the right place.


idea? none

Things I currently run through the reverse proxy:

Decided off the bat not to bother with Etherpad, as I haven't looked under the hood and don't know how I'd do domain validation at all. Figured the others would be doable.

Generating certs

Ran the letsencrypt Docker container. The current docs run it with -p 80:80 443:443 and the auth command and no plugins. I left out the ports and used the manual plugin, as I can't conceive of how it would do domain validation it across containers, so I'm not even going to try rig that up:

sudo docker run -it --rm --name letsencrypt \\\\\\\\
  -v "/etc/letsencrypt:/etc/letsencrypt" \\\\\\\\
  -v "/var/lib/letsencrypt:/var/lib/letsencrypt" \\\\\\\\ certonly --manual

I gave it several subdomains, for each of the different apps I have running, and Worked through domain validation for all of them (putting a file in .well-known).

Down to three subdomains, I (finally!) generated one cert for all of them. It stored the files (cert.pem, chain.pem, fullchain.pem and privkey.pem) under the name of the first one on the list (in /etc/letsencrypt/live/sub.mydomain.tld).

Installing certs

I had it on good advice that if I restarted the proxy container I wouldn't need to restart all of the other containers. The instructions for SSL in the docs for the proxy say:

$ docker run -d -p 80:80 -p 443:443 -v /path/to/certs:/etc/nginx/certs -v /var/run/docker.sock:/tmp/docker.sock:ro jwilder/nginx-proxy

It also says "The certificate and keys should be named after the virtual host with a .crt and .key extension". I had .pems so I threw caution to the wind and renamed:

Put them in a directory that I mounted to the proxy container when I relaunched it (above command). Given the rename, the proxy is supposed to just find them I guess?

Failure 1: port 443 is already in use. o.O I couldn't figure out what is already using it, but later wondered if Gold is maybe sneakily hijacking it. Otherwise I found this docker bug which may be it but I am in no position to upgrade docker right now (I know, I know). Faced with imminently needing to relocate to somewhere without wifi and not being able to cope knowing my Etherpad was down, I relaunched the proxy container as above, without -p 443:443, but still with the path to certs. Whew, everything came back up.

Except... The first subdomain, the one that the certs are named after, is now serving Gold, not the Apache container it was supposed to point to. The subdomain that is supposed to be serving Gold is also serving Gold. Neither are using the correct cert.

So... that's where I'm at.


If you've read this far and have the remotest clue about any of these puzzle pieces, please let me know all the things I'm getting totally wrong.

See also: HTTPS: Not a terrible experience

🏷 https cert cpanel hacking https letsencrypt ssl tls