In recent years, increased interest in the Professional judgment and Decision Making (PJDM) of outdoor instructors has focused on experts. This paper builds on earlier work, exploring the components and development of PJDM in mid-career outdoor instructors. The study conducted and thematically analysed semi-structured interviews with nine senior instructors working for Outward Bound Trust (the Trust) in the UK. Findings included two over-arching themes: (1) a Hahnian approach to development, in line with the philosophies that underpin the Trust's work; and (2) practical wisdom: the synergy of contextual comprehension and appropriate options. We conclude that these mid-career outdoor instructors' decision making is dependent on high levels of situational awareness, situational demands, and availability of appropriate options as a course of action. We further identify a philosophical chain between the Trust's ethos, instructor development, and adaptive expertise. These skills develop through a process akin to a cognitive apprenticeship within the Trust's community of practice.