I don't think a rule can do that. Automatically requesting receipts is an
all-or-nothing setting. Either you request a receipt on all outgoing
messages or you don't. It can't be tailiored to specific recipients, as far
as I can tell.
I don't think that you can set it to only request it from one particular
person, but to set your read receipts for all your outlook messages, Go to
tools>options>preferences tab>email options>tracking options, then check the
appropriate box(es).
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