SSL setup for two droplets, one on main domain and second on subdomain

What is the recommended practice for setting up SSL with Let’s Encrypt where one droplet hosts WordPress ( and a second droplet hosts Discourse under a subdomain (


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Normally I’ll install certbot on each server and then generate the certificates as per norm via CLI.

When it comes to multiple servers, if you generate them on the main host, you may run in to issues with the challenge aspect of the process.

It really depends on whether you use the certonly option or one of the plugins (i.e. for Apache / NGINX).

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As mentioned above you could install certbot in each droplet.

Another approach is to setup your main droplet (or spin up a new 512mb droplet) with NGINX if not already using it as a load-balancer/reverse-proxy with SSL Termination. This gives the benefit of managing all of your SSL certificates in one place.

Thanks @jtittle. My goal is to keep things simple, so two independent certificates it will be.