Not a dumb question at all :) The topic you should look into are wildcard domains. There seems to be a bit more set up involved, you can read about it in their docs: https://caddyserver.com/docs/automatic-https#wildcard-certificates One thing you should be aware of is that not all applications work as expected being served under multiple domains.

Peter Thaleikis You get unlimited bandwith + serverless functions. Their DNS propagation is blazing fast and it auto-generates deployments for all your branches (tho I think that this works with netlify as well)

Peter Thaleikis Ah forgot you were a PHP guy. Have you taken a look at vercel?

What service are you managing them with?

Amazing, switched from a Ghost blog self-hosted with Caddy to Hashnode. The branding is a bit aggressive but for what you're providing a good trade-off. Would be amazing if you guys added a Ghost importer :)

Hi Damon, do I understand correctly that you're installing Caddy on server-a? The php_fastcgi directive replaces the reverse_proxy directive. Do you have a specific reason you want to keep serving the PHP site via nginx? If you want to proxy to nginx, you don't need the php_fastcgi, but should be able to only use reverse_proxy. If you want to switch completely to Caddy on server-a, you could try out the example in their docs. I would also review their documentation on the php_fastcgi directive . As my knowledge of php is fairly limited, I don't know how this is usually done on either nginx or caddy. Hope this helps.