The legalities around incidents in outdoor education (OE) are undeniable, and ignorance is not a defence. Using case study analysis specific to legal literacy, we extend this analysis to include the “7 Rights” framework and add two additional rights for consideration, referred to as the 9 Rights. This discussion organizes what is publicly available on the Toronto District School Board (TDSB) outing, and death of Jeremiah Perry, and draw insights from the decision of the Ontario Superior Court of Justice in the subsequent criminal negligence trial. We present our analysis and recommendations, based on the 9 Rights. By exploring pertinent legal terminology, relevant to this case, the 9 Rights guides risk analysis for trip planning, in-field risk assessment, and risk management. The unfortunate crux of this discussion, and many OE incidents in Canada, is that the law enters the learning equation only after something goes wrong.