In this paper we describe a creative sentencing research project that arose from infractions at an oil sands in situ facility. We briefly outline some root causes of the infractions, key features of the industry context at the time, and lessons for regulatory compliance. While there were some contextual factors such as general industry turbulence, regulatory uncertainty related to a new technology and an industry wide personnel shortage that contributed to the conditions that resulted in these infractions; we also identify more fundamental causes of the compliance failures in this case. We find that a weak management of change process, weak operational compliance tracking and a weak culture of compliance were all at the root of this particular failure. We stress the importance of building a culture of compliance, viewing compliance as a journey and managing the cognitive load of compliance as important elements in ensuring compliance.