Technology often promises increased safety in the form of reduction of human errors. However, there is a dynamic relationship between technological solutions to risks and human behavior. The attempt to design out a persistent pattern of accidents caused by human error can lead to a new, perhaps unanticipated, and possibly even more dangerous pattern of accidents caused or exacerbated by the technology. For this reason it is essential that products liability law proceed from a systems approach, not considering product design and user error in isolation. This article argues that a systems approach to accidents involving technologically advanced products, taking into account the relationship between product design and foreseeable carelessness by users, is essential to ensuring that the law of products liability does not have a negative impact on the underlying goals of this area of law, including the promotion of increased user safety, innovation in product design, and the affordability of useful products. The article uses, as a case study, two accidents involving the Boeing 737-Max jetliner. The Max design incorporated a design feature intended to prevent accidents caused by a pernicious observed pattern of human error. When it failed to function as intended, the result was disaster. Should the blame for these accidents be placed on the manufacturer, for flaws in the design of what was intended as a safety feature? Or should the flight crews be blamed for failing to handle a foreseeable glitch that they were trained to deal with? Complex systems involving interactions between machines and human operators pose a challenge to the usual approach of torts and products liability law of focusing on ex ante incentive creation because of the dynamic relationship between, on the one hand, features of the product’s design and information provided by the manufacturer that are sensitive to patterns of foreseeable user error, and, on the other hand, user behavior that is shaped by the product’s design and the information provided by the manufacturer. The doctrinal and theoretical analysis developed in the context of the 737-Max accidents will be important in other emerging technology contexts, such as the liability exposure of manufacturers and drivers of semi-autonomous cars.