Based on an ethnographic study within the road maintenance sector, this paper explores the occurrence of rule violations in industrial settings subject to a high level of regulation, and is specifically concerned with operatives' risk perceptions in relation to health and safety rules and with management strategies for their successful mitigation. The study contrasts two different, but related, types of risk. Firstly, it considers those aspects of health and safety where the limits of 'best practice' working are insufficient to eliminate or control major sources of risk, and secondly, it looks at risks the known outcomes of which are underestimated as a result of being delayed or indeterminate. The paper considers the sources of rule violation, such as operatives' sense of self-efficacy; the need for heedfulness as well as compliance; and the dangers of risk displacement and the creation of a 'second order' focus.