Wildcard SNIs not being matched

No problem. And thanks.

I’ll spend a little time to make sure the policy matching works correctly.

What is happening in your case is with the automation policies. Those matchers are taken literally, since you can actually have a certificate with a subject of *.shine.caddy.test.shinenelson.xyz (a wildcard certificate), vs. "all certificates for subdomains of shine.caddy.test.shinenelson.xyz".

I suppose we could try lumping them together, i.e. doing an exact match first, and if not, then trying a wildcard match… not sure if that would break anything though… probably not?