Objective: The purpose is to analyze the issues and challenges faced by education students in secondary education who conduct part of their training in a pedagogical project aimed at delivering socio-educational workshops in juvenile facilities for adolescent offenders. Theoretical Framework: The research is based on studies on initial teacher training (ITT) and the clash between university training and classroom reality, as well as critical perspectives on the standardization of teaching performance, which do not consider the unpredictability, uncertainty, and high complexity of teaching in confinement contexts. Method: A qualitative methodology is chosen. The sample consists of 23 students and 14 graduates. Data is collected sequentially over an academic semester through the writing of various narrative and a semi-structured interviews with students. In the case of graduate students, a discussion group is conducted. Results and Discussion: The results, consistent with the literature, indicates that the students often reproduce a standardized education that clashes with the complexity and unpredictability of confinement contexts, leading to feelings of fear and a search for security in specific indicators. Research Implications: The results have implications for the teacher training programs that aims to provide training for highly complex and uncertain contexts, which requires breaks and openings in people's imaginaries and subjectivity. Originality/Value: This study contributes to the field of practical and didactic teacher training for them to perform in highly uncertain and complex contexts.