SBS 2011, SMTP not sending to outside addresses


  • Background:  SBS 2011, new install (no migrations), new domain, new FQDN.

    I have email setup and working perfect for OWA.  I can send and receive messages (to everyone) without issue from OWA.  I also have iPhone clients connecting via ActiveSync without issues that can send and receive (to everyone) without issue. 

    I am trying to setup an IMAP client (Outlook 2010) on a computer that is not connected to the SBS domain (e.g.  I have enabled IMAP and the services are running correctly.  I had to change the authentication mode to basic to get the authentication to work for Outlook 2010.  The problem I am having is getting SMTP to send messages from my Outlook client.  I can send messages to (internal) without issues but when I try to send to nothing works.

    After searching this forum and other forums I thought it might have been the connector setup on port 25 and the ISP blocking traffic.  I then followed this blog to setup another connector for port 587.

    My mail client can connect to the SMTP and seems to work but the message never gets delivered to the outside email address nor do I see it listed in the delivery reports.  I have checked the queue looking for a message or error message but either I am looking in the wrong place or the message is not there.

    Can someone help me figure out why my messages are not getting delivered to outside addresses?

    Bryan Brannon
    Wednesday, March 09, 2011 1:19 PM

All replies

  • Why are you using IMAP to connect Outlook 2010 to the SBS if the client PC is in the local network? You should just configure Outlook to connect directly to Exchange directly on the SBS.
    Regards, Boon Tee - PowerBiz Solutions, Australia -
    Wednesday, March 09, 2011 1:40 PM
  • Because the Outlook 2010 and client machine used to connect to this is on a different domain.  Let's say my SBS 2011 domain\username is: CONSOTO\Bryan  My client machine is hooked up to another domain ANOTHERCOMPANY\BryanB and does not seem to want to connect to the SBS native exchange.  Is that possible?

    Also, I used Outlook 2010 as example.  The same example could be used for Thunderbird or Entourage.

    Bryan Brannon
    Wednesday, March 09, 2011 1:58 PM
  • You can use 'outlook anywhere' but would reccomend the use of a Commercial CA Certificate (godaddy, verisign etc)


    Robert Pearman SBS MVP (2010)
    Thursday, March 10, 2011 1:23 PM
  • That is a work-around that works but that does not solve my problem.

    There is a problem with the server and am looking for someone to help with solving the SMTP issue for IMAP clients.

    Bryan Brannon
    Thursday, March 10, 2011 3:45 PM
  • Ok No problem.

    Have you looked in the message tracking logs to see if that turns up anything?

    I havent tried IMAP on 2011, ill see if i can give it a try.

    Robert Pearman SBS MVP (2010)
    Thursday, March 10, 2011 3:57 PM
  • Thank you!

    I am not sure where to look for the messages.  What is strange is that in my IMAP client, the messages sends fine to other users within my domain.  I just can't "relay" out to an external domain like  I never get an error that it could not send just no email message in the account.

    Bryan Brannon
    Thursday, March 10, 2011 4:14 PM