I have a problem which I have been trying to solve for weeks but cannot find a working solution.
I have a webserver with 5 different domains. I am using Outlook365 as mail server so no local email addresses are created. Because the PCI scan I need to use encrypted authorization for the local SMTP server (mailenable standard) I have SSL certificates installed for every domain. I only need to send mails by the shopping cart applications (VPcart9), all other email traffic goes directly to Outlook365 (mx record points to outlook using an external DNS server) So I only need to use the local SMTP server for the outgoing mails from the applications.
First I tried to send to Office directly from the applications using smtp.office365.com port 587, could not make it work.
Then I tried to smarthost relay to office via the local mailenable SMTP server, also used MEroute, made a connector in office to accept relay from the used IP addresses, I can let this work for one domain but not multiple domains because the SMTP server is configured for one domain cert so let’s call it domain1 and is using the cert for domain1, if mailing from domain2 the cert doesn’t match because mailenable SMTP server is using the cert for domain1 and mail rejected. Using the local SMTP server to send directly without Office365 gives the same cert difference problem.
Maybe somebody can help me out?
