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The accidental untying of a shoelace while walking often occurs without warning. In this paper, we discuss the series of events that lead to a shoelace knot becoming untied. First, the repeated impact of the shoe on the floor during walking serves to loosen the knot. Then, the whipping motions of the free ends of the laces caused by the leg swing produce slipping of the laces. This leads to eventual runaway untangling of the knot. As demonstrated using slow-motion video footage and a series of experiments, the failure of the knot happens in a matter of seconds, often without warning, and is catastrophic. The controlled experiments showed that increasing inertial effects of the swinging laces leads to increased rate of knot untying, that the directions of the impact and swing influence the rate of failure, and that the knot structure has a profound influence on a knot's tendency to untie under cyclic impact loading.