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I experienced the following error : User (email@example.com) The server has tried to deliver this message, without success, and has stopped trying. Please try sending this message again. If the problem continues, contact your helpdesk. Diagnostic information for administrators: Generating server: dc1.domainPtyLtd.local firstname.lastname@example.org #550 4.4.7 QUEUE.Expired; message expired ## Here is the fix. a little background regarding the mail. I created a custom rule for users inside our company who uses a different mail account(ie email@example.com + firstname.lastname@example.org)so that their incoming and out going mail get routed via a custom receive connector. This caused me some major headaches because i was receiving the above mentioned error for about a week and no mail came into the system. Here is what i did. 1: I removed the custom rule and recreated with the following setup 2: I only enabled Anonymous users on the permissions. 3: Under scoping added the IP of the external mail profile 4: Inside XCH powershell add following command : Get-ReceiveConnector "External Frontend EX2013" | Add-ADPermission -User "NT AUTHORITY\ANONYMOUS LOGON" -ExtendedRights "Ms-Exch-SMTP-Accept-Any-Recipient" After this my headache was gone. took a week but fixed my issue. Hope this helps you.