Great post with lots of detail! Unfortunately I only have UI access to the web client so can't investigate any further than that and am not sure I can help that much in this instance. You might need to contact SmartBear support here for help.
Of the two issues you've shown with screenshots, I notice that the execution times for the Pass/Fail and Fail/Pass are 1 minute apart from each other and wonder if that's got something to do with it. Perhaps a caching issue in Jira or Zephyr. If you're able to replicate the issue by running two tests close to each other you might be able to observe the behaviour and figure out what's happening - would love to know the answer if you do!
Good luck!
Thank you for the direction to support I'll contact them and see if I can gather some more information.
Also I think you might be on to something too with the times being so close, I might look at those a little closer in the database and see just what the timestamps are saying in there and see if there is any time overlaps that aren't apparent when looking at it in the UI. 😀
