make “Read Receipt†based upon recepient (in contacts) not Global

[MatJ]

When I want to send an email with a “Read Receipt†or a “Delivery
Receiptâ€, I only have 2 options: 1) to set it to always send these (Global,
which for anyone that sends a lot of emails is murder) or 2) to always
remember on an individual email message basis to go into Options and check
these 2 checkboxes...
I would really like it if I could set these 2 options on each Individual
Person (from within Contacts) that I wanted to use these for on a regular
basis (like the Payroll Clerk, or my boss, or whoever) because I want to know
when and if they have read my messages.
This would be a very useful additional feature!!!

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[neo [mvp outlook]]

You didn't mention what version of Outlook you are using, but I would check
the rules wizard to see if you can create a "send" rule that accomplishes
what you want.