The aim of this thesis is to investigate the situated subjectivities of the experiences of Forest School (FS) practitioners, in their journeys from training to initial practice. The research explores the impact of FS training, environmental and socio-cultural influences upon the practitioners and how their practices adapt in context. Eight in-depth case studies of FS trainee practitioners were undertaken over a period of two years (2010-12) using multiple qualitative methods. The analysis is in three parts; on practitioner identities, approaches and contexts. The thesis contributes three new conceptual models to outdoor pedagogical research. The concept of eco-social identity frames the ongoing construction of self. The FS adult role is theorised as a connector, engaged in dynamic role processes. The analysis of practitioner approaches in context uses Shared Space; an ecosystemic frame of practice and agency. Further analysis of practitioners’ experience of team contexts draws on theoretical lenses on role, socialisation and norms from Goffman and Foucault. Team relationships became positioned in either conflict, collaboration or congruence. The study contributes new insights into the impact of FS training and the influence of socialisation and subjectivity in the application of outdoor pedagogy. Early life experience, nature-society relations, and passionate purpose motivated the practitioners. Adult-to-adult interaction affected practice outcomes significantly, with strong disparities in setting teams regarding values and ethos, team interest, controls and standards in setting practices, curriculum pressures, setting aims, and site provision and care. The results imply that collaborative partnership and a whole team approach are effective strategies for ongoing practice, and tokenistic practice is a destructive strategy.