How to Troubleshoot SMTP Relays on Windows Servers

Details

To better understand how to guide a customer or partner in their troubleshooting of a SMTP Relay issue outside of ShoreTel, here are the basic routing steps of a SMTP Relay using a smart host from Director to email server:

  1. In Shoreware Director under Sites, the SMTP Relay should be set to the IP address or server name of the Windows Server you want to be the SMTP Relay. Typically, this can be the HQ server as shown in the following example:

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  2. On the HQ Server, Open IIS 6.0 Manager.

    a. Right-click the SMTP Virtual Server and click on Properties.

    b. NOTE: First, look at the Messages tab to verify various messaging limits placed on the SMTP messages. This will be important when moving voice mailboxes between ST VM servers. Mailboxes are packaged up into a single SMTP message and sent via the SMTP Relay to the destination VM server. Messages larger than the set limits may result in a portion of the VM messages being lost.

    Move users in groups whose total VM box used capacity is smaller than the message size limit set in the SMTP Relay or change the message limits as appropriate, aligning with the Exchange Server message limits.
     

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    c. Next, look at the Delivery tab >Advanced button, to verify the Smart host destination. Depending on the customer’s email infrastructure, this could be the name of the Exchange Server (as shown below), IP address of the Exchange Server, a specific IP address associated with a Receive Connector on the Exchange Server, or internal DNS alias which could route “round robin” to redundant perimeter mail filters that is in turn handed off to the Exchange Server.

    On the same Delivery tab > Outbound Security button, (not shown here) only Anonymous Access is selected as well as the Access tab > Access Control > Authentication button, Anonymous Access is also checked.
     

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  3. On the Exchange Server (e.g. Exch 2007) that the Smart host is pointed to above, open Exchange Management Console > Server Configuration > Hub Transport, and look at the Receive Connectors tab for the appropriate Receive Connector which matches the criteria of the HQ server or where the SMTP Relay is located via IP address or IP address range.
    The HQ in this example is in the subnet 172.17.2.0/24.

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  4. Under the same properties window, verify that the Permission Groups tab has Anonymous users checked at the very least.

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  5. If any changes were made, the SMTP service will likely need to be restarted on the Windows Server where the changes occurred. Use services.msc instead of the services plug-in in the IIS GUI to ensure it restarts properly.

  6. When testing the SMTP Relay, use the following folder locations as reference to monitor

    the progress or issues related to any test messages.

    • C:\Windows\System32\Logfiles\SMTPSVCI\ [SMTP Logs on the SMTP Relay]

    • C:\Inetpub\Mailroot\Queue\ [Outgoing Mail Queue on SMTP Relay]

    • C:\ShoreLine Data\VMS\Message\ [System Storage location for VM messages]

    • C:\Inetpub\Mailroot\Badmail\ [Unsuccessful Send Mail Folder on SMTP Relay]

  7. To Enable SMTP logging for IIS 6.0 or 7.0 for testing the SMTP Relay:
    • Right-click the SMTP Virtual Server and click on Properties in IIS

    • On the General tab, check Enable logging and click on the Properties button

    • Go to the Advanced Tab

    • Under Extended logging options, check all options except the last 3 check boxes (i.e. User Agent, Cookie, and Referer).

    • When testing is complete, uncheck Enable logging and click OK.

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Article: 000001985