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Receiving hundreds of Outbound Mail Failure messages in Exchange 5.5 admin mailbox daily

I have an Exchange 5.5 SP4 Server. I am getting the following messages in the admin mailbox (hundreds a day):

Outbound Mail Failure

The following recipients did not receive the attached mail. Reasons are listed with each recipient:

MSEXCH:IMS:XXXXXX:DDDD:CHCNT05 0x80040C02 (00050311) Maximum receipt headers exceeded (possible mail loop).

The message that caused this notification was: All email is addressed to addresses that are no longer in the GAL.

Eventually the NDR is returned but that takes days sometimes. The event logs show Evevt ID of 4098 and 12071 max hop count exceeded.

I've checked everything and can't figure it out. Any suggestions?

If it only happens when you SEND messages the two most likely things are either DNS has been changed, or you've changed the method used to deliver mail. Perhaps it was "Forward all..." and now it's "Use domain name system (DNS)" (or vice-versa).

This behavior occurs because Internet Mail Service is connecting to itself in an attempt to deliver the message. One of the following should resolve this for you:

  • Add an MX record for .com in DNS specifying the proper mail host.

  • Add .com in the "Specify by E-Mail Domain" area on the Connections tab of Internet Mail Service properties specifying the proper mail host.

  • On the Routing tab of Internet Mail Service, configure .com to route to the correct destination mail host.

    Hope this helps.

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