Smart Attachments (a paid add-on) looks like it should do that and more. One of the bullet points from the overview:
Disclosure! We're friends with the guys at Stiltsoft, and that's how I happen to know of this particular plugin, but I haven't used it personally.
Hey everyone! My name is Sarah Schuster, and I'm a Customer Success Manager in Atlassian specializing in Jira Software Cloud. Over the next few weeks I will be posting discussion topics (8 total) to ...
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