The purpose of the present study is to examine how risk is perceived and managed in one wilderness-based therapeutic program for at-risk teenagers, through the lens of high reliability theory. This theoretical framework has emerged through analyses of (usually technologically complex) organizations that are perceived as high-risk, yet appear to largely avoid negative outcomes. While outdoor adventure therapy programs for at-risk youth remain unstudied within the framework, I propose that they may fulfill some criteria associated with so-called high reliability organizations (HROs). A case study approach, applying a number of principles identified by Weick and Sutcliffe (2007) as key to organizational reliability, is taken. I use a set of surveys by the aforementioned authors along with semi-structured interviews to elicit front-line staff perspectives on risk, risk tolerance, risk management, and related communication and decision-making, thereby exploring the extent to which these principles are relevant and applicable in this setting. The characteristics and principles identified in the chosen literature on high reliability organizing appear to fit relatively well with this organization’s risk management practices, as experienced and described by its front-line staff, however individual responses vary. The principles appear most relevant to risks related to client behaviours, less so to risks related to the wilderness environment, suggesting the framework used here may be usefully applied in a range of organizations where management of risky behaviours is key.