Outlook 2016 - Missing Sent Items, how to diagnose

Oliver Dickins 1 Reputation point
2020-08-06T08:54:38.06+00:00

Hello.

I have an issue where by a customer performs some tasks in Outlook and another third party program which looks like the following.

  • User opens Outlook 2016
  • User opens Third Party Program (Pegasus Opera)
  • User sends mass emails from the Third Party Program as invoices
  • User notices the items being sent and see them appear in the "Sent Items" folder within Outlook
  • Then, around 2 minutes later, the items all disappear from the "Sent Items" folder
  • Exchange Server (Exchange 2010) - Get-MessageTrackingLog - shows the items being sent
  • Items don't appear in Deleted Items, or the "Recover Deleted Items" folders.
  • Export-Mailbox, doesn't yield any results either.

The above can be replicated and has occurred twice now, but I'm unsure really how to diagnose this issue.
I've enabled Outlook advanced logging and took a look at what appears in the ETL files when you delete from Sent Items however there is so much chatter I'm unsure really what I'm looking for.

Any Outlook peoples got any tips to diagnose the above?

Thanks!

Outlook Management
Outlook Management
Outlook: A family of Microsoft email and calendar products.Management: The act or process of organizing, handling, directing or controlling something.
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  1. JeffYang-MSFT 6,241 Reputation points Microsoft Vendor
    2020-08-07T08:30:16.71+00:00

    According to your description, it seems that you are using Exchange email account when sending emails. As I know, when exchange users accidentally delete an item from Outlook mailbox, you can often recover it via Recover Deleted Items From Server. So, please try to check your Recover Deleted Items From Server feature and see if you can find those disappeared items.

    To further confirm your issue, it is suggested to log in to your web mail and see if you can find those disappeared emails.

    User sends mass emails from the Third Party Program as invoices.

    Does this issue only happen to emails sent from your Third Party Program?
    To check if the issue is related to your Outlook client or your email account, it is suggested to exit other programs ,run Outlook alone and send test emails to see if this issue can be reproduced. You could also send emails from the web mail and see if there is any difference.

    If this issue can also be reproduced when directly sending emails from your Outlook client, I'm afraid that the issue might be mostly related to your Outlook client. As I know, there could be some add-ins in your Outlook client that cause this issue, so it is suggested to start your Outlook in safe mode (Press Win + R, type “outlook /safe”, press Enter.) and see if the issue continues.

    If Outlook can work fine without other programs, I'm afraid that the issue might be mostly related to your Third Party Program. Please try to troubleshot from the perspective of the Third Party Program and see if could helps.

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  2. Oliver Dickins 1 Reputation point
    2020-08-07T09:28:55.237+00:00

    Thanks JeffYang.
    I have some time Monday to check over a few things.
    In the mean time;

    • Recover deleted items from Server feature does not list the missing items
    • The items do not appear in OWA
    • The issue only occurs when running from the Third-Party program

    I will try the safe mode.
    I'll also try creating a new profile on Monday.