Conduct disorder is characterized by both habitual aggression as well as non-aggressive rule-breaking behavior. While a large body of research has focused on aggressive behavior to date, the subtype of non-aggressive rule-breaking behavior is poorly understood. The current study represents a first attempt to directly assess decision biases toward rule-breaking behavior, their motivational salience, and the association with interpersonal factors in conduct disorder. Participants (n = 20 children with conduct disorder and n = 20 healthy controls) played a video game with the goal to deliver a hot pizza by bicycle to a marked location on a two-dimensional city map. In each trial, participants decided whether to use the regular route (streets) or opt for a potential shortcut that was either permitted (bicycle lane) or prohibited (park). The efficiency of the shortcut was parametrically varied to assess individual decision functions. Consistent with our hypotheses, group differences emerged only when taking a shortcut represented a rule violation (park condition), with the conduct disorder group committing significantly more rule violations than controls. Furthermore, conduct disorder children showed a substantial frequency of rule violations even in the absence of shortcut related gains, indicating a pronounced insensitivity towards sanctions. Importantly, this tendency was associated with self-reported impulsivity and rule violations in real life.