Issue
In a hybrid Exchange environment of Exchange 2013 and Exchange Online, mail sent to a specific distribution group was only delivered in some mailboxes.
Investigation
The issue had the following characteristics
- Sender is an Office365 user
- Distribution group contains both O365 users and on-premises users
- Mail sent to this Distribution group is only received by O365 users
The error in Exchange Online was:
Reason: [{LED=550 permanent failure for one or more recipients (emailaddress:550 Empty envelope senders not allowed)
So, what does this “550 Empty envelope senders not allowed” message tell us? Apparently, the on-premises mail gateway rejected the message, because envelope senders was missing.
According to this Microsoft KB-article, the values ReportToManagerEnabled and ReportToOriginatorEnabled should not be both $false
Solution
To verify this thing was the issue, run the following command in your On-Premises Exchange Powershell:
Get-DistributionGroup -Identity dg-test | fl Displayname,*Report*
DisplayName : dg-test
ReportToManagerEnabled : False
ReportToOriginatorEnabled : False
As you can see, both values were set to False. This caused the error.
To adjust, run:
Get-DistributionGroup dg-test | Set-DistributionGroup -ReportToOriginatorEnabled $true
or
Get-DistributionGroup dg-test | Set-DistributionGroup -ReportToManagerEnabled $true
To verify all your distribution groups, run:
Get-DistributionGroup | ft Displayname,*Report*
