Reviving this thread as I'm experiencing the same behavior. I'm new to using the ruler but I've created ~10 quests and for the life of me "Step On" does not work. I'm also having the same trouble with "Give" for a specific item. For instance, a unique item with wurm id 12345678, I set the Give option and the "Current item" which I do have selected. When I give the item - nothing happens. The trigger doesn't fire, the effect never happens and the quest stays active.
Any advise would be great - this is preventing some cool quests