automx hostname sending, and letsencrypt certificates

[David Mehler]

Hello,

I'm noticing two issues that might be a contributor to the reason
autoconfig/autodiscover is not working for my domain.

The first is I'm using a letsencrypt certificate, (connecting with
outlook 2010), and I keep getting prompted if I want to accept the
key. I say yes then later I am prompted again. First issue, I thought
letsencrypt certificates were trusted and I should not get this
message.

I am using a SAN certificate. The order is something like:

domain.com www.domain.com test.domain.com blog.domain.com
mail.domain.com autoconfig.domain.com autodiscover.domain.com

Do the certificates for autoconfig/autodiscover need to be their own
certificates no SAN (Subject Alternative Name)?

Second issue, in attempting to send an email tonight I noticed in the
maillog of my server that the hostname is not an fqdn, that the client
is sending. My email server is configured to reject non fqdn helo
clients, can this be got around? I'm using Postfix 3.1.

Thanks.
Dave.