&gt; this is how it should work. Very nice.<p>Thanks for your comments; glad you like the way we integrated it!<p>&gt; Does it automatically bundle domains and request a single certificate with SANs?<p>No, as it turns out, SAN makes the auto-management code highly complicated, since names could overlap in different certs, etc. It also complicates renewals and gives more room for error (e.g. 49 of the domains verify but 1 fails, so the cert can&#x27;t be renewed). So I&#x27;ve opted not to support SAN certificates for the automatic HTTPS feature. But you can of course still issue your own SAN certificates and use those.<p>Right now, Caddy reloads itself when it renews certificates, but as of Caddy 0.8.2 (slated for release any day now), Caddy will do it all in-process, no reloading.