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Outgoing email shows successful delivery report, can't find it in sent or deleted items?

Posted on 2014-09-18
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Last Modified: 2014-09-22
Exchange 2010SP3 on 2008R2:  We have a user that sent an email, the email was confirmed received by people inside and outside the organization, and I have a successful delivery report.  However, neither the user nor myself can locate a copy of the email in Sent or Deleted items, only a prior version in Drafts.  Is there a way to locate this email server-side, given that I'm able to generate a successful delivery report?
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Question by:sbumpas
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by:Simon Butler (Sembee)
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Have you looked in OWA? It isn't unheard of for the problem to be with Outlook - usually a corrupt OST file.

Simon.
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by:sbumpas
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Yes we did check there, but no luck.
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by:Simon Butler (Sembee)
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If you cannot see it in OWA, then the message isn't in the database.
That is perfectly possible - usually an indication of a network issue or corrupt OST file. OWA is showing the live information from the database, there will be nowhere else it can be seen.

Simon.
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by:sbumpas
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Any idea how/why that would happen?  And why it would generate a successful delivery report if the message is gone?
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by:Simon Butler (Sembee)
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When you send an email, two things happen.
1. The message is sent.
2. The message is copied in to the Sent Items folder, then synchronised.

If the second step fails, then you don't have a copy of the message.

Simon.
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by:sbumpas
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If the 2nd step fails, how can i troubleshoot to ensure it doesn't happen again?
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by:Steven Wells
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Could the message have been sent from someone else who has SEND AS permissions on that persons mailbox?

The message will be sent, and the email be in the sender's mailbox, not the person who the email was from.
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by:sbumpas
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Unfortunately no such premissions exist on this particular user.
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Simon Butler (Sembee) earned 500 total points
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The second step is very unusual to happen - I think I have seen it two or three times in my entire career where it has happened once. Therefore there isn't anything you can do to stop it from happening again, because it is unlikely to happen again.

If it does happen again with the same user, then that can suggest an underlying problem with their workstation, network configuration or hardware, or even a corrupt OST file.
Frequent occurrences with the same user are more common, but again impossible to predict or monitor because they will still be unusual. If they do happen with a high amount of frequency then you should be able to get in to a position where you can replicate it on demand and troubleshoot that way.
The standard test for Outlook issues is to get the user to try another machine. If the problem does not follow (which is the most likely) then the issue is with the workstation.

Simon.
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