I have a certificate with 4 SAN entries added in the ordered as listed:
But if I look at the certificate the order listed in the SAN field is the opposite, so starting with “autodiscover.company.be” end ending with “mail.company.nl”.
Is this because of how Certify handles the request, or Let’s Encrypt?
Normally this shouldn’t be an issue, however Microsoft did a terrible job with their SMTP server service. This service tries to find a suitable certificate and doesn’t offer any configuration, and I read somewhere that it will only check the first entry of the SAN field.