Custom rule for Out of Office (OFF) response

Georges Carraha 1

Hi,

We have a problem getting a custom rule for an "Out of Office" (OFF) response to work as expected for an Exchange server 2013.

For the user we created the rule as follows:

Apply this rule after the message arrives
have server reply using <subject>
except if the subject contains 'reply' or 'failed' or 'undeliverable'

The rule works for senders within the domain but not for external senders. We have configured the Exchange to allow sending automatic forwards and automatic replies to the Internet.

If we run the command "Get-RemoteDomain Default | fl AllowedOOFType, AutoReplyEnabled, AutoForwardEnabled" we get the result

AllowedOOFType : External
AutoReplyEnabled : True
AutoForwardEnabled : True

Any idea what could be causing the rule not to work for external emails?

Regards,

Kael Yao-MSFT 37,691 Reputation points Microsoft Vendor

2022-01-27T06:34:38.973+00:00

Hi @Georges Carraha

Please run get-messagetrackinglog in EMS to check the mail flow of the autoreply message.
Would you see some events like FAIL or DROP? Or would you see the SENDEXTERNAL event?

1 answer

Georges Carraha 1 Reputation point

2022-01-27T14:55:23.373+00:00
Hi,

I ran the following command:

Get-MessageTrackingLog -ResultSize Unlimited -Start "1/27/2022 12:00AM" -End "1/27/2022 11:59PM" -Sender "<sender>" | Sort-Object MessageId | Format-Table EventId, Source, Sender, Recipients –AutoSize | out-string -Width 1000

When someone inside the domain sends an email to the user, the custom rule generates the OFF response and the message tracking below. In this case the <sender> is the user for which the custom rule was set and the <recipient-internal> is the person who sent the email to the user:

EventId Source Sender Recipients ------- ------ ------ ---------- RECEIVE MAILBOXRULE <sender> <recipient-internal> DELIVER STOREDRIVER <sender> <recipient-internal> HAREDIRECTFAIL SMTP <sender> <recipient-internal> AGENTINFO AGENT <sender> <recipient-internal> RECEIVE SMTP <sender> <recipient-internal> SEND SMTP <sender> <recipient-internal>

When someone outside the domain sends an email to the user, the OFF response generates the message tracking below:

EventId Source Sender Recipients ------- ------ ------ ---------- AGENTINFO AGENT <sender> <recipient-external> RECEIVE MAILBOXRULE <sender> <recipient-external> SEND SMTP <sender> <recipient-external> TRANSFER ROUTING <sender> <recipient-external> HAREDIRECTFAIL SMTP <sender> <recipient-external> RECEIVE SMTP <sender> <recipient-external>

Regards,
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Kael Yao-MSFT 37,691 Reputation points Microsoft Vendor

2022-01-28T03:34:17.987+00:00

Hi,
Thanks for the information.

Below is a screenshot when testing in my lab (the Outlook inbox rule works fine for external recipients):

To me the problem here is that it is supposed to be a SENDEXTERNAL event instead of SEND if the recipient is external.

If you send a message directly to the same external recipient, can it be received correctly?

Kael Yao-MSFT 37,691 Reputation points Microsoft Vendor

2022-02-02T08:41:55.57+00:00

Hi @Georges Carraha

I am writing here to confirm with you how thing going now?
If any updates on this issue, please feel free to post back.

Georges Carraha 1 Reputation point

2022-02-03T18:27:32.56+00:00

If I send a message directly to the same external recipient, it is received correctly.

From an external email address (<external>), I sent an email to the user who has the custom "Out of Office" (OOF) rule (<user>). On the user's Exchange server I ran the following command:

Get-MessageTrackingLog -ResultSize Unlimited -Start "1/27/2022 12:00AM" -End "1/27/2022 11:59PM" -Sender "<user>" | Sort-Object MessageId | Format-Table EventId, Source, Sender, Recipients –AutoSize | out-string -Width 1000

The result is as follows:

As you can see the OFF rule does generate the OOF email. However, on the "external" Exchange server the OFF email does not arrive. I ran the command below and comes up empty.

Get-MessageTrackingLog -ResultSize Unlimited -Start "2/3/2022 1:00PM" -End "2/3/2022 11:59PM" -Recipient <external> | Sort-Object MessageId | Format-Table Timestamp, EventId, Source, Sender, Recipients, MessageSubject -AutoSize | out-string -Width 1000

The user with the OFF sends a message to the external email address. On the user's Exchange server I ran the command again. The result is as follows:

On the "external" Exchange server the email does arrive. I ran the command again and the results is as follows:

Regards,

Kael Yao-MSFT 37,691 Reputation points Microsoft Vendor

2022-02-04T08:56:15.68+00:00

Thanks for the update!

According to the information, the recipient side also has an Exchange server ("external" Exchange server).
Does this issue also occur on other external senders besides from this external Exchange server (Outlook.com,Gmail,etc...)?

If not, are the two Exchange servers in a same domain, or sharing a SMTP domain name(configured internal relay domain)?
If adding Get-transportservice before Get-MessageTrackingLog..., what would the result be like?
(Get-TransportService | Get-MessageTrackingLog -ResultSize Unlimited -Start "2/3/2022 1:00PM" -End "2/3/2022 11:59PM" -Recipient <external> | Sort-Object MessageId | Format-Table Timestamp, EventId, Source, Sender, Recipients, MessageSubject -AutoSize | out-string -Width 1000 )

Georges Carraha 1 Reputation point

2022-02-04T12:14:50.143+00:00

Hi,

The problem also occurs if we sent an email to that person from a hotmail account. The hotmail account never receives the OOF message.

The two Exchange servers are not in the same domain and network.

I did you test with the Get-transportservice command. The results are the same.

Get-TransportService | Get-MessageTrackingLog -ResultSize Unlimited -Start "2/4/2022 7:00AM" -End "2/4/2022 11:59PM" -Sender "<user>" | Sort-Object MessageId | Format-Table Timestamp, EventId, Source, Sender, Recipients, MessageSubject -AutoSize | out-string -Width 1000

When an email is sent from hotmail to the users Exchange account, the OOF message is generated by Exchange but never arrives at hotmail. See the tracking below.

If we sent an email from the user's Exchange account to the hotmail account, it does arrive. See the tracking below.

Regards,

Kael Yao-MSFT 37,691 Reputation points Microsoft Vendor

2022-02-08T09:28:27.013+00:00

Please enable Protocol log on the send connector(if you don't have specific send connectors for specific recipients, enable log on the send connector which sends emails to the internet)
and have a check of the process in the logs.
Default log path: %ExchangeInstallPath%TransportRoles\Logs\Hub\ProtocolLog\SmtpSend

Please note that the timestamp in the log is UTC time.

Georges Carraha 1 Reputation point

2022-02-08T18:35:37.19+00:00

Hi,

I enabled protocol logging on the send connector.

I'm not familiar with the output but based on what I see, I cannot find any line which would explain why the custom OOF rule is not working.

Below are the lines in the log related to the OOF response generated for user (user-email) to the external recipient (external-email). The email is not received by the recipient.

Below are the lines when the user sends an email to the external recipient. The email is received by the recipient.

Regards,

Kael Yao-MSFT 37,691 Reputation points Microsoft Vendor

2022-02-09T07:01:40+00:00

Thanks for the information.

From the screenshot it seems the messages are sent to the local Exchange server's port 25 (127.0.0.1:25) , which is supposed to the external mail server's port 25.
Please post the detailed settings of this send connector and accepted domains on your Exchange server.

I suppose normally it should be like:
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