[j_s]

I think caddy supports automagically combining multiple domains on LetsEncrypt certificate requests. It is possible to set it up as a proxy just to get certificates but be aware of rate limit issues, especially if a domain expires or otherwise becomes invalid.

https://caddyserver.com/

I was trying to use it temporarily as the simplest way to get a multi-domain LetsEncrypt cert on Windows, but ran out of time attempting to convert the resulting certificate format into something I could take back to IIS.

Those securing custom subdomains are looking forward to January 2018 when wildcard certificates arrive. https://letsencrypt.org/2017/07/06/wildcard-certificates-com...

[ngrilly]

By design, Caddy doesn't support SAN certificates:

https://github.com/mholt/caddy/issues/831

[j_s]

Thanks for clearing up my confusion. From the discussion there it looks like this project might meet OP's needs:

https://github.com/containous/traefik

[ngrilly]

Yes, it looks like Traefik handles SAN certificates from LE.