Installing the IIS SMTP Service on SBS 2008 Breaks Mailflow

Installing the IIS SMTP Service on SBS 2008 Breaks Mailflow

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[Today's post comes to us courtesy of Shawn Sullivan]

Exchange 2007 is not designed to co-exist with the IIS SMTP service on the same server. This is unlike Exchange 2003, which depends on IIS to provide the SMTP service. If you install the SMTP service on SBS 2008, you will cause a conflict that can result in the inability to receive incoming email from the Internet.

One symptom of this is the receipt of an NDR by external senders:

Delivery has failed to these recipients or distribution lists:

administrator@contoso.com
The recipient's e-mail system can't process this message at this time. Microsoft Exchange will not try to redeliver this message for you. Please try resending this message later, or provide the following diagnostic text to your system administrator.

Diagnostic information for administrators:

Generating server: SERVER.contoso.local

administrator@contoso.com
#< #5.3.5> #SMTP#

5.3.5 means a mail-loop condition is detected.

Exchange will not write a protocol or message tracking log for these incoming connections since it never actually receives them.

Other indications can be found when you telnet to the server and read the SMTP banner and the list of verbs. The default SBS Internet Receive Connector will appear as so:

clip_image002

Note the external FQDN on the banner, the maximum message size, and the verbs.

If you receive the internal FQDN of the server in the banner, a different maximum message size, a Version number, and extra SMTP verbs, then you are hitting the IIS SMTP service:

clip_image004

NOTE: Your results can vary if you have manually edited any of these settings. This example assumes that you have accepted the defaults.

To resolve this issue, you must uninstall the SMTP Server feature from the Server Manager console and reboot the server:

clip_image006

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  • PingBack from http://www.ditii.com/2009/04/03/sbs-2008-installing-iis-smtp-service-breaks-mailflow/

  • [原文来自Shawn Sullivan] 在设计上,Exchange 2007是不能与IIS的SMTP服务共存的。这一点与Exchange 2003不一样;Exchange 2003要依赖IIS的SMTP服务来发邮件。如果您在SBS

  • Is possible to make it work changing the tcp port of smtp?!? I need to send mail from a network printer to a specific mail box and when i set the ip of sbs as smtp relay i get an authentication error.

    I have tryed to set authentication on the printer but i get authentication error, the user exist in exchange but seems something is wrong!

    Or is possible to install smtp server of iis with another tcp port and make coexist smtp server and exchange?!