It can be difficult to think of teaching critically as a social responsibility within settings that do not appear closely related to larger social values, practices, and problems. The author uses an interpretive ethnographic method to study criticality in the classroom within a job reeducation program designed to prepare laid-off factory workers for employment in clerical positions. The theoretical framework introduces the idea of multiple criticalities in contexts examined at the intersection of biography and culture--that is, working with the individual and social simultaneously and seeing them in relationship. The author examines ways criticalities were fostered, forms they took, and pedagogies that reflected classroom practices. Finally, some of the problems and contradictions of teaching for criticality in this context are examined.