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I'm wanting to write a scriptrunner behaviour that checks to see if the Sprint field is getting updated and make a different specific field required if it's updated. I know this will work when editing an issue via Edit but will this also work when dragging and dropping an issue between sprints on a Rapid Board? Will the user be prompted with the required field if they update the issue in this way via a Rapid Board?
No, this will only work when you have a form/screen with editable fields. Either on Edit or during a Transition.
If you have a transition with a screen, moving between columns on the active board will trigger that form and the behavior script will take effect.
Now, if you change the sprint via drag/drop (true also of bulk or api changes), the change will happen regardless of the behaviour, but the next time a form is presented (either edit or transition) then the specific field will be flagged as required (if visible on that screen, especially relevant for trimmed downed transition screen) and other modifications will not be possible until the missing field is addressed.