MS IIS SMTP Relaying email after Exchange Back-end Server is rebooted

Posted on 2006-04-28
Last Modified: 2011-10-03

  I have an IIS SMTP Front-end Relay Server in a DMZ, running on Windows 2003.  I also have a back-end Exchange 2003 server on Windows 2003.  I am running into an issue when the Exchange Server is rebooted.  After the reboot, the relay server queues message and doesn't relay them, until I restart the SMTP service.  It might start relaying after a few hours, but I'm not sure.  On the Exchange Server I have an SMTP connector, but I don't think that has anything to do with it.  I think that's only for outgoing.  Is there a setting on MS IIS to reattempt sending to the back-end server?  I can not see any settings in the IIS Manager --> local computer --> Default SMTP Virtual Server --> Domains window that shows the smart host forwarding property.  I know there are settings for Outbound delivery on the SMTP Birtual Server Properties page.

Question by:dauyeung
    LVL 35

    Expert Comment

    > I know there are settings for Outbound delivery
    For the IIS SMTP, the relay to the exchange server is "outbound", therefore these settings are responsible for the reattempt.

    Sett this to 15 Min (default) for the first attempt, but also note, that the server will count the attempts during the exchange is booting. If this happens on a transfer attempt, it maybe that the second or third attempt time is affected as well. So check these setting.

    Author Comment

    However,  even when a new email comes in and the exchange server is back up, it doesn't send.  It's almost like the whole server stops sending.  I thought that those settings you talked about were per message.  You would think that a new message coming in would be sent fine, but it is not.  Everything queues.

    Thanks for the quick response,
    LVL 35

    Expert Comment

    You are right, these settings are mail based.

    Have a look here:

    Means: Have you installed SP 1 for Win2003?

    Author Comment

    Yes, SP1 is installed.

    It is possible there is nothing wrong and it is because of my Outbound Delivery Settings.  They are

    1st - 15 min / 2nd - 30 min / 3rd - 60 min / subsequent - 240 min

    The question becomes how do I balance internal try responsiveness to external retries.

    i.e.  Would it be bad to set these to the following?

    1st - 5 min  / 2nd - 10 min / 3rd - 15 min / subsequent - 15 min

    This leads to another question:
    Is there a tool, like Exchange System Manager that would allow viewing of the queue and the message state?  (Exchange System Manager --> Exchange --> admin groups --> first admin groups --> servers --> exchange-server-name --> queues)
    LVL 35

    Accepted Solution

    Timing: It depends, how often it happens, that mails are temporary undeliverable. You server gets a little bit more load. You can change the settings and look what happens, have a look at the task manager and service times now and after the change (let the server run a few days). Then you can compare the times against the idle time to see, how much more load you get, but I assume, it will not so heavy.

    > This leads to another question:
    You mean for IIS? No, the SMTP service so not have the stages, the exchange has. SMTP is the basic transport and exchange also uses the W2K3 SMTP service in general, but has more stages, where mails are handled (the different queues). But these queues are not file based, nevertheless the exchange uses the same folder (under Exchsvrv\mailroot\vsi 1)

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