I am having an issue with sending message to specific domains and getting a 4184.108.40.206 error. The messages come back to the users as Delivery Delayed in their Outlook and I see the 4220.127.116.11 in the Queue as well as the undelivered messages. I have examined the MX records and verified using online tools such as MX Lookup tool. I have turned off our AV and tried it with no luck. When I telnet 25 to the SMTP servers in question I get no response from them. The only thing that has changed is we upgraded from SBS2003 to SBS2008. Our inbound mail is filtered by a 3rd party spam tool but all outbound mail goes direct from us.