I'll still post a screenshot, but upon further digging I might have got some misinformation. Apparently Orion is properly creating an event on the service status, but that event doesn't match any alert chains. Thus, I think my problem is more that none of my alert categories (stock or otherwise) are alerting on if a service is in the "Stopping" state; only if it is actually down and the process is not found.
In the attached screenshot, the service is currently running as normal. I've asked to get a screenshot of when the issue is ongoing.
