This chapter draws on the work of Vygotsky (see Daniels, 2001; van der Veer and Valsiner, 1991) and Bernstein (2000) to examine the pedagogic dilemmas in teachers’ work as they attempt to re-engage learners with school knowledge in non-traditional education contexts. Mainstream schooling has failed the students who attend these educational contexts. Consequently, the emphasis on relevant curriculum, fl exible implementation, inter-agency collaboration, life-skills development and readiness for work aims to provide an alternative or nontraditional context designed specifi cally to meet the needs of these students (de Jong, 2005; de Jong and Griffi ths, 2006).