Certificate from GoDaddy is in place, I have removed esmtp inspection from our Cisco ASA, and hybrid mail is flowing from Office 365 to our on prem Exchange 2013 server. When trying to send mail to a mailbox migrated to Office365 I am receiving the dreaded '451 5.7.3 STARTTLS is required to send mail".
Since our MX is pointing to a 3rd party mail filter I changed the on prem connector created by the hybrid config wizard to relay mail through 'ourdomain-com.mail.protection.outlook.com'
I am also able to telnet directly from our Exchange server to ourdomain-com.mail.protection.outlook.com 25. An ehlo shows the STARTTLS verb IS available.
Kind of hitting a wall here. I would greatly appreciate any insights from the community!