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IME Caddy will not do wildcard domains "by default" if you just configure sub.domain.com {} for everything. It will try to create a unique cert for each. You have to specifically configure it to use a wildcard cert.
Yeah it will, if you have even a single reference to a wildcard, preferably as one of your first entries in your caddyfile.
https://caddyserver.com/docs/automatic-https
You can literally get a wildcard cert by putting in the following entry, before any other routing logic: