Viewing adolescents as a distinct group, having special learning needs, is a relatively new trend in educational discourse. This chapter focuses on adolescents who were never enrolled or dropped out from school due to extreme conditions of deprivation. The position that is argued here is that educational planning for these out-of-school adolescents has to be identified afresh in a holistic manner. The interventions need to be designed for addressing the processes of marginalisation, which reinforce their deprived status in society. This chapter is divided into two broad sections. The first section focuses on understanding ‘adolescents’ and identifying their learning needs. For this, it draws upon Sandhan’s experience of working with adolescents over the past fifteen years, both directly and as a support organisation for community-based initiatives. The second section attempts to evolve an approach for educational planning, which could respond to the identified needs, more especially of out-of-school adolescents from marginalised groups.