Unless you actually add something to the workbook to flag which records have been included in an email, then test the flag state, there is no way your macro can differentiate between those records for which an email has been sent and those for which one hasn't. Of course, if the macro is run periodically (e.g. every 28 days), you could add logic to the code to exclude records for which the expiry date has passed - but that's still not going to resolve everything if the macro is run early and will create other problems if it's run late...

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Cheers,
Paul Edstein
[Fmr MS MVP - Word]