Do you need to always request read receipts for some addresses you send messages to, but not all?

Create an After sending rule.

1. Open Rules Wizard
2. Select the option to start from a blank rule
3. Choose the after sending option
4. Enter the condition(s) and click Next
5. Choose the Action to request read receipts
6. Save the rule and Ok your way out of the Rules Wizard

Now every message you send that meets the condition of the rule will have read receipts requested.