Education is conceived as a multifaceted, multidimensional and complex process of social transformation; nevertheless, schools operate within a passive environment that restricts the learning of young people from vulnerable contexts. This qualitative study explores the pedagogical strategies of four educators from one public institution in Valdivia who work with students who have been associated with episodes of law infraction. Analytical procedures rely on content analysis following the logic of grounded theory and In-depth Interviews. From a biographical perspective, the present study identifies the pedagogical strategies of these autonomous and optimistic educators to favor the construction of modifying active environments in this vulnerable context. It also seeks to generate new lines of research on critical pedagogy in vulnerable educational contexts, strengthening and enriching the competencies of educators from Mediated Learning Experiences.