Ever since I moved my hosted exchange email account from Godaddy to Microsoft I have had issues with mail that is destined to or originates from another Exchange user on a different domain.
Firs some of the mail destine for me was rejected as undeliverable. That user who was sending me mail was also on a GoDaddy hosted Exchange account. I called GoDaddy and they deleted a "cached" address that apparentlky was still directing to the old MX server. That issue got fixed.
Now I am having issues sending a message to another user on their on Exchange Acct. Here is what their IT team said they saw:
From what I can see, Andy is using hosted Outlook to relay his mail for him. This is the bigfish.com domain. Although he appears to have a working SPF/TXT record set up, I’m not sure that we’re checking that at the firewall. If we aren’t, then the messages would definitely look like a domain spoof and might be rejected for that reason.
I don’t see any MX records for totherescuedfw.com, which might be another problem; when validating the source of SMTP traffic, spam filters will often do a DNS lookup to check for MX and/or PTR records. My requests to look up MX records are meeting with server timeouts, which complicates things a bit – the records might exist, but we aren’t seeing them. However, I can still look up SPF records, so I know that the DNS servers for the domain aren’t down. Even though mail is being handled for Andy’s domain by his hosted Outlook service, he should still have MX records that point to that service.
Any ideas?
Routing problems aside, Andy is still able to get messages in to you that report that there is a problem. This would indicate that a) the routing isn’t consistent on his messages coming in, b) there is some content filtering going on on our end, or c) some other contingency.