This chapter encompasses approaches to learning and instruction that situate learning in problem-solving contexts with a focus on Problem-based learning and Productive Failure. We focus on these two approaches because they both begin with a problem to be solved and learning occurs in context, as learners engage with novel content. We consider how these instructional approaches are complementary by using Kapur’s (2016) notion of productive success and productive failure. Key instructional design characteristics and supports are described for each approach. Empirical support for both Problem-based learning and Productive Failure is summarized along with describing roles for technology. We conclude by articulating directions for future research, and deriving implications for the field of the learning sciences.