Out of office / Automatic Office Reponses - Delivery failed

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,

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

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.

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.

What does message trace show on your account?

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

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.

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.