Interest-driven learning has become a focus of attention in educational research and school education. With a guiding framework proposed from literature study, this chapter discusses how interest could be used as intrinsic motivation for learning, how interest could be built upon the notion of play, how interest-driven learning environments could be linked to the informal learning paradigm, how making orientation can help students regain their individual agency and cultivate in students the knowledge, skills, and means to accomplish their designs. Case studies on how low-progress students in Singapore have learnt from such interest-driven learning environments are also discussed.