I figured this one out, but thought I would post in case someone else bangs their head against this in the future.
Scenario:
User wrote an Automation rule with a trigger of Issue Transitioned to [StatusX]. It's not getting triggered (doesn't even appear in the automation log).
Added a second status to test - that one triggered.
Verified there wasn't another status with a similar name / etc.
Took a close look at the workflow... this particular workflow has multiple phases. The team using it has the issues move something like this: Open --> Review --> Approved (DONE) --> User submitted paperwork (Reopen) --> Build --> Done.
The status we were triggering on was the one that re-opened the issue. It's was set to trigger an "Issue Created" event.
Which meant that automation didn't see it as a transition. It saw it as a create.
Options to fix:
- Change the Event type in the workflow (up to the users)
- Change the trigger to Issue created + condition (JQL: status = [StatusX])