This one is a bit out there.
Jira sends out notification emails. In Outlook or similar I can request an 'email read' notification when I send a personal email. Any wild ideas how I might achieve something similar with a Jira system email?
Well, the feature you describe is specific to Exchange, a proprietary mail server and client. It doesnt translate well into the world beyond. Similarly Gmail has a service for business users, but this is visible only in the gmail UI, again, tight dependency between service provider and mail interface.
I doubt very much any generic solution will ever exist to do this as there is not standard the clients can conform to to indicate they have actually read the message.
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