Answer
The workflow observation panel not showing entries for background-job-created records doesn't necessarily mean the workflow didn't fire — observation visibility in the UI has been unreliable depending on platform version, so check the async workflow tracking table directly for evidence it ran. To confirm definitively whether the event is actually triggering independent of the observation UI, build a minimal start→action→stop workflow that does something externally verifiable (like an email or a REST call to a mock endpoint) and see whether that fires for the background-job scenario — this isolates whether the issue is the trigger itself or just the observation UI's visibility of it.