"554 5.4.14 Hop count exceeded - possible mail loop" NDR for outgoing email that's sent to an on-premises application in Exchange Server

Applies to: Exchange Server 2016Exchange Server 2013

Symptoms


Consider the following scenario:

  • You have a parent domain, contoso.com, that you have added as an accepted domain to an on-premises Microsoft Exchange Server 2016 or 2013 environment.
  • You have an on-premises application server domain, such as app.contoso.com, that is a subdomain of the parent domain.
  • The parent domain is configured to accept email messages from domains such as *.contoso.com.
  • You try to send an email message to the on-premises application through Exchange Server.

In this scenario, the message cannot be sent. Instead, it loops between the Exchange Edge Transport server and Exchange Online Protection (EOP). Additionally, you receive a non-delivery report (NDR) that resembles the following:

554 5.4.14 Hop count exceeded - possible mail loop

Cause


This issue occurs because the Exchange Edge server cannot associate the SMTP address space for the application as a subdomain to the accepted domain. This is true even though the accepted domain is configured as a parent domain.

In this scenario, the subdomain would be part of the address space in the EdgeSync - Inbound to SiteName send connector.

Resolution


To fix this issue, follow these steps:

  1. Add the subdomain as an accepted domain. To do this, run the following command:

    New-AcceptedDomain -DomainName app.Contoso.com -DomainType InternalRelay -Name app.contoso.com
     
  2. To have the newly added accepted domain synced to the Edge servers immediately, run the following command:

    Start-EdgeSynchronization

    Alternatively, wait for the changes to be synced to the Edge servers.