I have added a requirement to the Add Flag and Comment screen to require the comment to flag an issue. This will generally prevent "Why was this issue flagged?" from being asked over and over again.
Everything works great when you right click an issue in the list view and then select flag: the screen pops up, comment is required, everything is working as intended. However, when you click the "Actions (...)" icon in the detail view and then select "Add Flag" the flag gets added without ever showing the comment screen.
We are using Jira Classic projects
Hey Chris - Yes, that's the behavior that has happened for as along has I have been using Jira Cloud. You could submit a request for clarification if you like:
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