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Outlook Resending Old Sent Items
Emails previously sent months ago are sent again.
Affected site uses Exchange 2007 (SBS 2008) and Outlook 2007 and Outlook 2010.
This has been randomly going on for years and we never really found a solution out there.

Narrowing it down to the Computer (Email Account) responsible was easy and we further investigated the issue.

Looking in the Outlook Folder C:\Users\Username\AppData\Local\Microsoft\Outlook we found a bunch of Temp Files (0K in size) corresponding to the same amount of sent Emails.
These files begin with "BIT" with some examples shown here:


Out of "suspicion" that the Outlook OST File or Profile was corrupt, we turned off Cached Mode (Cached Exchange Mode) and verified that there were no Sent or Outbox Items pending to be sent.

Without doing anything else, we re-enabled Cached Mode and opened Outlook - suddenly over 50 previously sent Emails suddenly appeared in the Outbox about to be sent again!
So it's without doubt that there is corruption somewhere along the line and that "Cached Mode" is a major factor.

There is a lot of misleading info out there on DuckDuckGo (more so on Google) leading to Exchange as the cause.
For us it was not Exchange but Outlook.

Due to the age of Outlook a permanent fix is not going to be pursued - we are simply going to disable "Cached Mode" until executive decisions are made to upgrade the Office Suite.

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