A custom transition I have created has a post function which assign the issue to the reporter. My notification scheme has the Issue Assigned event set to notify the Current Assignee.
When an issue goes through the transition, it is rightfully assigned to the reporter yet no email is sent (to the reporter, ie the current assignee.) I have monitored the Mail Queue but nothing happens when I trigger the transition.
The Notification helper confirms that users should get the notifications and if I manually assing the issue to the user, they do receive an email.
You do not mention what "event" your transition fires.
The thing that causes an email to go out is a built-in listener which picks up events. Events are fired in several places, but these boil down to two types.
System events are fired by activity in Jira. These are fixed and unmodifiable - edit issue always fires updated, comment on issue fires comment, version changes fire the version related events, delete, move, log work, etc. Most relevant here is that the action "assign issue" (and assign to me) fires the "issue assigned" event.
Secondly, transitions fire events. That's a post-function on the transition and you can choose what event to fire.
I think the problem you have here is that you are assuming that "changing assignee during a transition" triggers "issue assigned". It does not. It's a transition. It *only* fires the event named in the post function. Whereas "manually assigning" fires "issue assigned"
This is a very long standing bug in Jira - the ideal fix would be for Atlassian to implement "fire issue assigned if assignee changes, irrespective of how it's changed".
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