>So I may assume that is why they are stuck in my spool, trying to deliver 20
>times.

The 20 attempts or whatever is definable by you in the SMTP panel, as 
is the interval between attemtps.

>However, I made a rule

where? the "rules" in Imail are teh filter rules that applies to 
incoming mail only, not to outgoing or relayed mail.

>that should delete these files based upon the sender.
>Why are they still in my spool?

see ispclean.exe in the manual for cleaning up spool files

Len


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