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Out of office / Automatic Office Reponses - Delivery failed

Hi,

Looking for some help on the following issue.

When an exchange mailbox has an Automatic reply set by outlook, teams, 365 portal etc, the outgoing email from 365 via sophos central to the external sender it fails. These have definitely previously worked.

Normal email flow (365>sophos central) works as expected with no issues. It is just the auto responses that fail.

Any help would be greatly appreciated.

Andy

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[edited by: Raphael Alganes at 10:38 AM (GMT -8) on 2 Feb 2024]

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0 Raphael Alganes over 1 year ago

Hi Andy,

Thanks for reaching out to Sophos Community.

Does this happen to all users or some users only? does the OOO reply issues happens only to external domains or also on internal? Could you also share NDR received by the sender.

Regards,

Raphael Alganes
Community Support Engineer | Sophos Technical Support
Sophos Support Videos | Product Documentation | @SophosSupport | Sign up for SMS Alerts
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0 Raphael Alganes over 1 year ago

Hi Andy,

Thanks for reaching out to Sophos Community.

Does this happen to all users or some users only? does the OOO reply issues happens only to external domains or also on internal? Could you also share NDR received by the sender.

Regards,

Raphael Alganes
Community Support Engineer | Sophos Technical Support
Sophos Support Videos | Product Documentation | @SophosSupport | Sign up for SMS Alerts
If a post solves your question use the 'Verify Answer' link.
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0 Andy Collins1 over 1 year ago in reply to Raphael Alganes

Hi Raphael,

This happens to all users that have OOO/ automatic replies on. It only happens sending to external domains, internal recipients get the OoO message as expected.

Unfortunately no NDR is received by the sender. Sending an email to the external recipient directly works as expected.

regards

Andy
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0 Slappy over 1 year ago in reply to Andy Collins1

Couple of questions:

Just to confirm this is not a shared mailbox and no external users are receiving email when OOO is enabled, right?

If you turn off OOO and user's external emails are sent successfully, right?

When checking outbound message trace on the user with the OOO enable, what are the results?

Per Microsoft......If you have OOO enabled, only one email will be sent to an external user during the OOO time period. So if one external user emails the user 5 time during the OOO is enabled, they will only receive one OOO message.
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0 Andy Collins1 over 1 year ago in reply to Slappy

Can confirm this is not a shared mailbox, the external recipient does not get the OoO email. It is shown as failed in Sophos Central.

External emails can be sent to the recipient with no issue without OoO on.

I have been testing with my own Out of office but the auto response always fails.
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0 Slappy over 1 year ago in reply to Andy Collins1

What does message trace show on your account?
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0 Andy Collins1 over 1 year ago in reply to Slappy

The trace from m365 shows the OOO message leaving the environment & being pushed to Sophos.

It is at this point that the message gets returned to Sophos as failed delivery.

Andy
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0 Raphael Alganes over 1 year ago in reply to Andy Collins1

Hello Andy,

Thanks for these details. I may suggest you to open a support ticket for this to be further investigated.

Kindly share with us the caseID once you have it.

Thank you for your time and patience and thank you for choosing Sophos.

Raphael Alganes
Community Support Engineer | Sophos Technical Support
Sophos Support Videos | Product Documentation | @SophosSupport | Sign up for SMS Alerts
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