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Members of a distribution group in Exchange Server may not receive email messages that do not specify a return path in Office 365 dedicated

Consider the following scenario in Microsoft Office 365 dedicated:
  • You have a distribution group that contains external mail contacts on a server that is running Microsoft Exchange.
  • You send an email message to the distribution group.
  • The header of the email message does not specify a return path.

In this scenario, some members of the distribution group may not receive the email message. Additionally, you do not receive a non-delivery report (NDR).

This issue occurs because some email servers do not accept email messages that do not specify a return path. This behavior is a method of spam prevention. For example, consider the following example Simple Mail Transfer Protocol (SMTP) conversation:

Server: 220 ESMTP Postfix
Client: HELLO
Server: 250 Hello, I am glad to meet you
Client: MAIL FROM: <>
Server: 250 Ok
Client: RCPT TO:

In this example, the recipient server rejects the email message because the message does not have a return path. 

Most frequently, the email message does not have a return path if both the ReportToManager and ReportToOriginator distribution group attributes are set to False, as follows:
Get-DistributionGroup | FL *report* ReportToManagerEnabled : False ReportToOriginatorEnabled : False
To resolve this issue, set the Return-Path value to one of the following values:
  • ReportToOwner (the manager of the distribution group)
  • ReportToOriginator (the originator of the email message)
Note Only one of these Active Directory attributes should be set to True. Setting both attributes to True produces unexpected results. 

To make this setting, set one of these attributes to True on the on-premises object (depending on the desired behavior), and allow for MMSSPP replication to the Microsoft Exchange Online environment. 


Article ID: 2618599 - Last Review: 11/26/2014 17:18:00 - Revision: 7.0

  • Microsoft Business Productivity Online Dedicated
  • Microsoft Business Productivity Online Suite Federal
  • Microsoft Exchange Online
  • Microsoft Exchange Online Dedicated
  • vkbportal226 KB2618599