I've seen similar behaviour when trying to place two preconditions in a row (i.e., PreCon-->AutoAction-->Status-->Precon-->AutoAction), in which case the second Precondition would fire, but only to make the following action available as a MANUAL action.
Can you try placing another status in-between (e.g., "In Progress") and have your actions/precondition come off that? Just as a test to break up the automated flow.
Thanks Brian, i'll give it a try
Have you made any headway with this? I am also struggling to find a way to cancel tasks based off the request being canceled.