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Out of office / Automatic Office Reponses - Delivery failed

Andy Collins1

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



Edited TAGs
[edited by: Raphael Alganes at 10:38 AM (GMT -8) on 2 Feb 2024]
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  • 0

    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
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  • 0 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

  • 0 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.

  • 0 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.

  • 0 in reply to Andy Collins1

    What does message trace show on your account?

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