Jump the rails Definition 1 of 2Pro Tip 1/3Negative Connotation Implies an unexpected negative turn in events or plans. Our vacation jumped the rails when the storm hit. Pro Tip 2/3Metaphorical Usage Used metaphorically to describe plans or processes that fail. The negotiations jumped the rails after the disagreement. Pro Tip 3/3Conversational Tone Common in spoken English and informal situations. It seemed like an easy task, but it really jumped the rails.