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  • Internet facing SMTP connector questions?

    Currently in the coexistence phase of my transition.

    When preparing for my transition I created a Internet facing SMTP connector on my legacy Exchange so mail would continue to flow while I installed the Hub Transport roll on my new server.

    I am at the step of creating an Internet facing SMTP connector on my new Exchange box, I am positive I have the connector configured correctly, using DNS MX records to route mail. In the Management Console I also have listed the Internet Facing SMTP connector that I created for my legacy Exchange.

    I have set the cost of the Exch2007 connector to 1 and the Exch2003 connector to 25. However when trying to send mail to an outside address from Exch2007 it get caught in the Queue with the error 451 4.4.0 Primary target IP Address responded with :"421 4.2.1 Unable to connect" Once I remove the Exch2007 SMTP connector mail continues to flow outbound through my legacy exchange server.

    Any ideas would be greatly appreciated.

    Thank you

  • #2
    Re: Internet facing SMTP connector questions?

    In the beginning you used your internet mail connector to route out mail. When you install 2007 it creates a routing group connector (RGC) between the 2003 and 2007. The 2007 mailboxes will use the RGC to send mail to 2003 which will send it out. The same RGC is used for inbound mail to the 2007 mailboxes from the 2003 server. When a 2007 send connector is created then, depending on your costs, mail can flow out of either one. Lowest cost wins.

    Does your 2007 send connector have a smarthost specified? Do you have any filtering on your outbound mail?
    cheers
    Andy

    Please read this before you post:


    Quis custodiet ipsos custodes?

    Comment


    • #3
      Re: Internet facing SMTP connector questions?

      Originally posted by AndyJG247 View Post
      In the beginning you used your internet mail connector to route out mail. When you install 2007 it creates a routing group connector (RGC) between the 2003 and 2007. The 2007 mailboxes will use the RGC to send mail to 2003 which will send it out. The same RGC is used for inbound mail to the 2007 mailboxes from the 2003 server. When a 2007 send connector is created then, depending on your costs, mail can flow out of either one. Lowest cost wins.

      Does your 2007 send connector have a smarthost specified? Do you have any filtering on your outbound mail?
      Im aware of the RGC, its just that when I create the send connector on exch2007 mail gets stuck in the Queue. No smarthost specified using DNS to route mail, also no filtering.

      Comment


      • #4
        Re: Internet facing SMTP connector questions?

        Sure, it was just background info.
        Can you telnet from the 2007 box to external mail servers successfully?
        cheers
        Andy

        Please read this before you post:


        Quis custodiet ipsos custodes?

        Comment


        • #5
          Re: Internet facing SMTP connector questions?

          Originally posted by AndyJG247 View Post
          Sure, it was just background info.
          Can you telnet from the 2007 box to external mail servers successfully?
          When using RCPT TO: [email protected] I get an error 550 5.7.1 Unable to relay

          A little background info, This machine is behind a PIX firewall, and port 25 is not open from the outside in to this particular machine.

          Comment


          • #6
            Re: Internet facing SMTP connector questions?

            This is from your 2007 box directly to a public mail server not to the server itself (just to clarify)?

            Make sure smtp fixup is turned off on the pix too. (no fixup protocol smtp)
            cheers
            Andy

            Please read this before you post:


            Quis custodiet ipsos custodes?

            Comment


            • #7
              Re: Internet facing SMTP connector questions?

              Originally posted by AndyJG247 View Post
              This is from your 2007 box directly to a public mail server not to the server itself (just to clarify)?

              Make sure smtp fixup is turned off on the pix too. (no fixup protocol smtp)
              Correct, I am using a local mailbox for the MAIL FROM command and a external mailbox for the RCPT TO command. I have also tested from my exch2003 box that goes through the same PIX and was able to successfully send the test email. But for some reason I cannot send from Exch2007.
              Last edited by benblank04; 21st October 2008, 15:40.

              Comment


              • #8
                Re: Internet facing SMTP connector questions?

                If you are using telnet then it should work from any machine assuming its public IP ends up as the same. If you can't telnet from the new 2007 server but you can from the 2003 server then I would imagine they are showing as different public IP addresses externally.
                How is your static setup on the PIX? Do you have multiple public IP?
                cheers
                Andy

                Please read this before you post:


                Quis custodiet ipsos custodes?

                Comment


                • #9
                  Re: Internet facing SMTP connector questions?

                  Originally posted by AndyJG247 View Post
                  If you are using telnet then it should work from any machine assuming its public IP ends up as the same. If you can't telnet from the new 2007 server but you can from the 2003 server then I would imagine they are showing as different public IP addresses externally.
                  How is your static setup on the PIX? Do you have multiple public IP?
                  I do have 2 external IP's but both machines do resolve to the same address.

                  Comment


                  • #10
                    Re: Internet facing SMTP connector questions?

                    If there is definitely nothing in between (like AV) then I am at a loss.

                    Can you post the results of the telnet from both the 2003 and 2007 boxes (change the personal info though).
                    cheers
                    Andy

                    Please read this before you post:


                    Quis custodiet ipsos custodes?

                    Comment


                    • #11
                      Re: Internet facing SMTP connector questions?

                      Telnet info from Exchange 2007 running on Server 2008
                      220 server07.domain.org Microsoft ESMTP MAIL Service ready at Tue, 21 Oct 2008
                      10:15:05 -0500
                      HELO server07.domain.org
                      250 server07.domain.org Hello [::1]
                      MAIL FROM:[email protected]
                      250 2.1.0 Sender OK
                      RCPT TO:[email protected]
                      550 5.7.1 Unable to relay

                      Telnet info from Exchange 2003 running on Server 2003
                      220 server03.domain.org Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at
                      Tue, 21 Oct 2008 10:19:11 -0500
                      HELO server03.domain.org
                      250 mail.domain.org Hello [192.168.154.XX]
                      MAIL FROM:[email protected]
                      250 2.1.0 [email protected]er OK
                      RCPT TO:[email protected]
                      250 2.1.5 [email protected]
                      DATA
                      354 Start mail input; end with <CRLF>.<CRLF>
                      ;
                      THIS IS A TEST EMAIL FROM EXCH2003
                      .250 2.6.0 <[email protected]> Queued mail for delivery

                      Comment


                      • #12
                        Re: Internet facing SMTP connector questions?

                        You need to telnet to an external host not to the Exchange servers themselves. We want to test smtp connectivity from the box itself without Exchange involved.

                        telnet gmail-smtp-in.l.google.com 25
                        It would probably be easier to find a host that shows you the info on screen though.

                        Does the message tracking show you anything about these emails in the queue as well? Any comments about the AV?
                        cheers
                        Andy

                        Please read this before you post:


                        Quis custodiet ipsos custodes?

                        Comment


                        • #13
                          Re: Internet facing SMTP connector questions?

                          Originally posted by AndyJG247 View Post
                          You need to telnet to an external host not to the Exchange servers themselves. We want to test smtp connectivity from the box itself without Exchange involved.

                          telnet gmail-smtp-in.l.google.com 25
                          It would probably be easier to find a host that shows you the info on screen though.

                          Does the message tracking show you anything about these emails in the queue as well? Any comments about the AV?
                          From Exchange 2007
                          Microsoft Telnet> open gmail-smtp-in.l.google.com 25
                          Connecting To gmail-smtp-in.l.google.com...Could not open connection to the host
                          , on port 25: Connect failed
                          Microsoft Telnet> open

                          The this exact command works from Exchange 2003, but also fails from my XP client?

                          Comment


                          • #14
                            Re: Internet facing SMTP connector questions?

                            Port 25 outbound is blocked on the Exchange box then (same for the XP client too). There are several possible reasons. McAfee AV blocks SMTP , the PIX may have outbound ACLs etc? Anything you can think of that may be in play?

                            If you post the PIX config (without personal info) I can have a look at that.
                            cheers
                            Andy

                            Please read this before you post:


                            Quis custodiet ipsos custodes?

                            Comment


                            • #15
                              Re: Internet facing SMTP connector questions?

                              Originally posted by AndyJG247 View Post
                              Port 25 outbound is blocked on the Exchange box then (same for the XP client too). There are several possible reasons. McAfee AV blocks SMTP , the PIX may have outbound ACLs etc? Anything you can think of that may be in play?

                              If you post the PIX config (without personal info) I can have a look at that.
                              It is the PIX for sure, I don't manage the PIX so I will have to talk to our Networking guy and let him know the situation.

                              Thank you for all your help Andy!

                              Comment

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