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Outlook 2016 - msg copied to Sent Items before actually being sent..? RRS feed

  • Question

  • Hi,

    My boss experienced a weird issue two days ago.  He sent .  On Monday he referred to a message with an attachment sent to two colleges, however it appeared that they never had received it.  He immediately checked his Sent Items folder and the message copy was there, with the correct Monday transmittal timestamp.  Later he double-clicked this message to open it, before he closed the message view by hitting the ESC button.  Immediately the message's timestamp changed to that of the moment he hit the ESC button (on Tuesday) and the message appeared in the addressees' mailboxes immediately after.

    How can it be possible that an outgoing message are copied to the Sent Items folder in Outlook 2016 before receiving an acknowledgement from the smtp server that it has been successfully forwarded to the recipients?  Note that both the sender and the recipients were licensed members of the same Office 365 domain, so we cannot blame a foreign email server.

    Thanks a lot for comments on this issue.  I need to know why we cannot be sure that a message actually has been successfully forwarded by the smtp server before it is being copied to the Sent Items folder.

    best regards

    Tor

    Wednesday, June 21, 2017 4:23 AM

All replies

  • Hi Tor,

    When the email was in Outlook Sent Items folder, did you check whether it was in the Sent Items folder from within OWA?

    In theory, Outlook doesn't move messages to Sent Items until it receives an acknowledgement from the SMTP server that the server has accepted the messages. If delivery doesn't happen, it's something after Outlook, not Outlook itself. Do you have any add-in or mail scanner which may scan your outgoing emails?

    Is the issue replicable in your boss's Outlook? If the issue is replicable, we may try to enable Outlook troubleshooting logging and see whether there is any errors in the SMTP transfer. For your convenience:

    https://support.office.com/en-gb/article/What-is-the-Enable-logging-troubleshooting-option-0fdc446d-d1d4-42c7-bd73-74ffd4034af5

    Hope this helps.

    Regards,

    Steve Fan


    Please remember to mark the replies as answers if they helped.

    If you have feedback for TechNet Subscriber Support, contact tnmff@microsoft.com.

    • Proposed as answer by Steve Fan Monday, July 3, 2017 9:46 AM
    Wednesday, June 21, 2017 9:39 AM
  • Hi Tor,

    How is everything going? Please feel free to post here if you find anything new or further assistance is needed.

    Regards,

    Steve Fan


    Please remember to mark the replies as answers if they helped.

    If you have feedback for TechNet Subscriber Support, contact tnmff@microsoft.com.

    Friday, June 23, 2017 1:57 AM