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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.
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
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Hi @Matt Goldstein ,
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.
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.
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.
Hi @Matt Goldstein ,
the response is not sent to either an Exchange Online, Exchange 2010 or external sender.
So you meant the auto reply can be sent to another mailbox hosted on Exchange 2016?
Have you checked the Queue Viewer to see if there are any clues?
By the way, from the output you shared above, I noticed that there's a remote domain for "Barracuda Message Archiver", was it added before the issue started?
So you meant the auto reply can be sent to another mailbox hosted on Exchange 2016?
I just tested between two mailboxes on Exchange 2016, but was unable to receive the automatic reply. The message does show in OWA while composing the email above the To field, but a full automatic reply email is not sent.
Have you checked the Queue Viewer to see if there are any clues?
I checked the Queue Viewer on the Exchange 2016 server directly after the test email was sent, but no messages were stuck. I did also check the Exchange 2010 Queue as well.
By the way, from the output you shared above, I noticed that there's a remote domain for "Barracuda Message Archiver", was it added before the issue started?
I believe I incorrectly censored this from the initial post, this remote domain is not a new addition and was part of the 2010 environment with auto replies working.
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/
Hi @Matt Goldstein ,
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 :-)