This chapter explores knowledge regarding professional practice in an emerging sub-group of outdoor professionals, namely the adventure sports coach (ASC). It also explores the domain-specific mechanisms, challenges, context and dynamics of the Professional Judgement and Decision Making process in high-level ASCing. The emergent field of ASCing encompasses a multiplicity of combined roles and diversity of function that generates high cognitive loads in the coaching process. The ASC role has emerged in response to increased demand for performance development in adventure sports. The ASC is unique in drawing on such a wide combination of skills, spanning areas such as risk management, risk–benefit exploitation, personal ability, pedagogic skills, leadership skills and domain-specific declarative knowledge in order to fulfil this complex and challenging role. Risk Benefit Analysis emerges as one process in which risk utilisation is aligned with the epistemological beliefs and pedagogy of the ASC. Irrespective of the available palette, the ASC must cope with a variety of challenges.