This chapter describes two different approaches to the care, education and rehabilitation of children in extreme circumstances. Children affected by war, traumatized, street children and orphaned young people. The work of Janusz Korczak is described. Korczak worked in the Warsaw ghetto with abandoned and orphaned children. He described strategies for a democratic education and meeting the children’s emotional needs. He wrote about the rights of children, which were later adopted by the United Nations. Anton Makarenko worked with delinquent and abandoned street children after the Russian Revolution. The chapter describes his work in two colonies, where an emotional involvement, a democratic system of governance and giving the children a sense of purpose and belonging are crucial ingredients for their rehabilitation. The work of these two authors is highly relevant today as there are many children in the streets all over the world, as well as many affected by wars and armed conflicts in many parts of the world.