If you have an issue with ShareFile Outlook plug-in sending old emails here after some more information for you
ShareFile Team has identified the cause of this behavior.
At startup, the ShareFile plug-in scans the Outbox for unsent messages with the intent of uploading attachments and sending messages with ShareFile attachments.
It then calls Outlook’s native send method all messages in the Outbox, instead of just those containing ShareFile attachments.
A fix for this will be included in the next release.
Until that version is released, please ensure there are no unsent items in the Outbox at the time the plug-in is installed and run for the first time.