Outlook sent messages not in Sent Items, and not delivered, they disappear

Some of our users are experiencing this
They compose a message and click SEND.
A few hours later they hear from the intended recipient no message was ever received.
The sender checks his/her Sent Items and sees no record of the message.
I check Exchange (2007) Tracker logs and see no record of the message.
It's as if messages disappear into thin air.
I know this is true for internal email, but i do not recall instances for external email.
Clients are mostly Outlook 2013, with only a few 2007 and 2010.  We are in the process of upgrading everyone to 2013.

Have you personally verified that this happens with your own two eyes?  I would hope that you're not posting here based on what a user has told you.
Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

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