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MattGoldstein-2956 asked YukiSun-MSFT commented

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

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 mail.companyname.com

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 testmailbox@companyname.com -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   testmailbox@companyname.com                                {[removed]@gmail.com}                          Automatic reply: External Test
 11/25/2020 4:00:54 PM  RECEIVE          MAILBOXRULE   testmailbox@companyname.com                                {[removed]@gmail.com}                          Automatic reply: External Test
 11/25/2020 4:01:07 PM  RECEIVE          MAILBOXRULE   testmailbox@companyname.com                                {[removed]@companyname.com}                          Automatic reply: Internal Test
 11/25/2020 4:01:07 PM  RECEIVE          MAILBOXRULE   testmailbox@companyname.com                                {[removed]@companyname.com}                          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 testmailbox@companyname.com | 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 - companyname.mail.onmicrosoft.com companyname.mail.onmicrosoft.com InternalLegacy             True
 Hybrid Domain - companyname.onmicrosoft.com      companyname.onmicrosoft.com      External                   True
 Hybrid Domain - companyname.com                  companyname.com                  External                   True

testconnectivity.microsoft.com
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

office-exchange-server-administrationoffice-exchange-server-deployment
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Hi @MattGoldstein-2956,

The issue I am seeing is with our first batch of users migrated from 2010 to 2016 and test mailboxes created on Exchange 2016.

Do you mean currently the issue is only affecting users migrated to or newly created on Exchange 2016, while the mailboxes on Exchange 2010 or Exchange Online can all send out automatic reply properly?
Would you please run the following command for a problematic auto reply message, then share the output here after removing all personal information?

Get-TransportService | Get-MessageTrackingLog -MessageSubject <subject> -Sender <mailbox address> -Recipients <mailbox address> |select timestamp,EventID,Source,ConnectorID |sort-object Timestamp

Besides, please try to test by creating a new remote domain for let's say gmail.com, enable its AutoReply and check if the out of office auto reply can be sent to gmail.com account successfully.
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Hi YukiSun-MSFT,

Do you mean currently the issue is only affecting users migrated to or newly created on Exchange 2016, while the mailboxes on Exchange 2010 or Exchange Online can all send out automatic reply properly?

Yes that is correct. If a user on Exchange Online sends to an Exchange 2010 mailbox the out of office message is received in the 365 users mailbox. If an Exchange 2010 user sends to an Exchange Online mailbox the out of office message is received. If a user with their mailbox on 2016, both migrated or freshly created, sets their out of office message the response is not sent to either an Exchange Online, Exchange 2010 or external sender.


[ 43953-msqa-exchangeoof-1.txt][1]


[1]: /answers/storage/temp/ 43953-msqa-exchangeoof-1.txt
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Would you please run the following command for a problematic auto reply message, then share the output here after removing all personal information?

When I ran the supplied command with a subject, sender and recipient added I received an error message. I removed the initial Get-TransportService and have that as the second block as well.

Ceating a new remote domain for let's say gmail.com, enable its AutoReply and check if the out of office auto reply can be sent to gmail.com account successfully.

I added a new remote domain for gmail.com and left the defaults of AllowedOOFType set to External and AutoReplyEnabled set to True. I did not receive an out of office response to the gmail address after disabling and reenabling the rule to clear the list of addresses that have had messages sent.

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MattGoldstein-2956 avatar image
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MattGoldstein-2956 answered YukiSun-MSFT commented

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 https://exchangemaster.wordpress.com/2014/08/21/oof-messages-not-being-sent-in-exchange-2013-cu5-environment/

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Hi @MattGoldstein-2956 ,

Great to see that you've got is resolved. Many thanks for your sharing! You can click the "Accept Answer" button under your post so that it will make answer searching in the forum easier and be beneficial to other community members as well. Thanks :-)

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