I'm a support enginer in CSS. I was working with a customer who reported a mail loop error for a specific domain like contoso.com. This error was only observed in large emails.  Yeah that’s really mysterious until you figure out that the mail loop is due to size restriction on the Send connector.  I thought this was curious enough to share.

Understanding the configuration and root cause of the issue:

I initially thought that this might have been the outcome of the Edge server being configured to use an external DNS server (a DNS server that resolves external hosts). Usually, when the Edge Tranport server is configured to use an external DNS, it resolves the domain name to the public IP addresses (generally pointing to itself, the exernal firewall, or the service provider) instead of a Hub Transport server in the Active Diectory site, causing a mail loop.

On reproducing the issue, I found out that the Edge Transport server was not configured to use an external DNS server. The environment I set up to reproduce the issue looked like the diagra below:

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Here's what happens in this scenario: When the Edge Transport server receives a 20 MB email from an Internet sender, it accepts it. The Edge Transport server has two connectors that match the address space - one for the address space contoso.com to the Active Directory site and one for the address space *. When making the routing decision based on all available connectors, the one from the Edge to Hub is not considered because of the size restriction (it has 10 MB size limit). The best match is the * connector from Edge to the Internet (Please go over the connector selection algorithm documented in Understanding Message Routing) which has a message size limit of 30 MB.

End result: The message is routed back to the Internet causing the message loop between the Internet and the Edge Server.

Based on whether the Send connector to the Internet is configured to use DNS or a Smart Host to deliver oubound mail, we will get one of the following NDRs:

If using DNS:

#554 5.4.4 SMTPSEND.DNS.MxLoopback; DNS records for this domain are configured in a loop ##

If using a Smart Host:

5.4.6 smtp;554 5.4.6 Hop count exceeded - possible mail loop> #SMTP#

The Solution

This behavior is by design and can be easily rectified by modifying the message size limit on the connector. Based on your requirement, you can choose either of the following options:

  • Set the MaxMessageSize parameter on the Receive Connector (which receives inbound mail from the Internet) to 10MB, so messages from the Interent are restricted to 10 MB.
  • Set the MaxMessageSize on the Send connector from Edge to HUB to 30MB, which will allow you to receive 30 MB messages from external senders.

Mystery solved! Thanks to Arindam Thokder and Scott Landry, who helped me with getting this ready for the blog!

Suresh Kumar (XCON)