Exchange 2010 to 2016 migration - Out of office auto responses not sent

Matt Goldstein 101 Reputation points

I have a hybrid domain configured in Exchange that currently consists of a single Exchange 2010 CAS server and a single Exchange 2016 server. A migration is in progress with mail flow and user access switched over to go through the Exchange 2016 server. The issue I am seeing is with our first batch of users migrated from 2010 to 2016 and test mailboxes created on Exchange 2016.

When a user configures an out of office message, either in OWA or Outlook - the auto response is not sent to anyone.

  • I can set the OOF message via the OWA, Outlook and Powershell without any error messages.
  • Once set I can view the config in all locations - OWA, Outlook or Powershell.
  • On both the 2010 and 2016 servers the internal and external virtual directories are configured as

The message tracking log shows these events with the subject of an auto response. But the response does not make it to the other users.

PS> Get-MessageTrackingLog -Sender -Start "11/25/2020 16:00:00" -End "11/25/2020 16:05:00"  
Timestamp              EventId          Source        Sender                                              Recipients                                          MessageSubject  
---------              -------          ------        ------                                              ----------                                          --------------  
11/25/2020 4:00:54 PM  RECEIVE          MAILBOXRULE                                {[removed]}                          Automatic reply: External Test  
11/25/2020 4:00:54 PM  RECEIVE          MAILBOXRULE                                {[removed]}                          Automatic reply: External Test  
11/25/2020 4:01:07 PM  RECEIVE          MAILBOXRULE                                {[removed]}                          Automatic reply: Internal Test  
11/25/2020 4:01:07 PM  RECEIVE          MAILBOXRULE                                {[removed]}                          Automatic reply: Internal Test  

When checking a test Outlook profile with mfcmapi, the PR_DELEGATED_BY_RULE field updates with email addresses of incoming messages.

Mailbox used for these tests does not have forwarding enabled:
PS> Get-Mailbox -Identity | fl DeliverToMailboxAndForward, ForwardingSmtpAddress, ForwardingAddress

DeliverToMailboxAndForward : False  
ForwardingSmtpAddress      :  
ForwardingAddress          :  

Remote Domains allowed OOF set to External and auto replies are allowed
PS> Get-RemoteDomain | ft -AutoSize Name, DomainName, AllowedOOFType, AutoReplyEnabled

Name                                           DomainName                     AllowedOOFType AutoReplyEnabled  
----                                           ----------                     -------------- ----------------  
Default                                        *                              External                   True  
Hybrid Domain - InternalLegacy             True  
Hybrid Domain -      External                   True  
Hybrid Domain -                          External                   True
Tested using the test mailbox on Exchange 2016 with the automatic reply option disabled. Used autodiscover, did not manually specify server.

Synchronization, Notification, Availability, and Automatic Replies - All tests pass
Outlook connectivity - All tests pass

Exchange Server Management
Exchange Server Management
Exchange Server: A family of Microsoft client/server messaging and collaboration software.Management: The act or process of organizing, handling, directing or controlling something.
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Accepted answer
  1. Matt Goldstein 101 Reputation points

    I would like to update that this is solved. I found that our Exchange 2016 server was in a group named ExchangeLegacyInterop that had two permissions, Accept Forest Headers and Accept Organization Headers set to Deny. This was possibly from reusing the hostname from an Exchange 2003 server.

    Fix found at

    1 person found this answer helpful.

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