Well, as far as I can tell, you cannot use a wilcard certificate (or multi-domain certificate) with Tiger. Going back to a single site got the web service working again…
Except…
Now I cannot enable it in Mail. It won’t work with the default even, that is created by the system, this appears in the logs:
May 1 11:33:43 mail imaps[639]: accepted connection
May 1 11:33:43 mail imaps[639]: TLS server engine: cannot load CA data
May 1 11:33:43 mail imaps[639]: unable to get private key from ‘/etc/certificates/Default.key’
For the “signed” certificate, it does the same thing:
May 1 11:28:41 mail imaps[553]: unable to get private key from ‘/etc/certificates/XXXXXXXXX.key’
May 1 11:28:41 mail imaps[553]: TLS server engine: cannot load cert/key data