Hi Mikel – Welcome to the Atlassian Community!
The part you’re missing is that adding Group custom field value to the “You’re assigned to a work item” notification only defines who receives that specific event. It does not make Jira fire the assignment event when your Group Picker field changes.
That system event is tied to the actual Assignee field.
For your use case, I’d use Automation instead:
Trigger: Field value changed
Field: your Group Picker field
Action: send the notification when the group changes
Automation supports custom fields with the Field value changed trigger.
Alternatively, if the group assignment happens during a workflow transition, you could create a custom event and configure the notification scheme so the Group Picker field is the recipient for that event.
So your Group Picker setup is valid — the main issue is that changing the group field does not trigger the “assigned” system event.
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