As far as I’m aware, as of 0.9 Caddy does support wildcard subdomains for SSL + virtual hosts.
Currently, I’ve added:
mysite.com, *.mysite.com {
...
}
But the logs only indicate a challange for the mysite.com address, and instead chose to host *.mysite.com on port http://*.mysite.com:2015. Is there something special to support wildcard SSL certificates or did I misread this as a new feature of 0.9?
Bingo - since Let’s Encrypt doesn’t issue wildcard certificates (yet, hopefully?), if you don’t know the hostname when you start the server you need to use On-Demand TLS to obtain certificates at request-time.