In this chapter, the author demonstrates how engaging with “productive failure” can be used to develop students’ capacity for complex problem-solving in the area of sustainable development. She demonstrates how this approach helps to encourage “productive failure” in students and thereby builds their capacity for complex problem-solving. Productive failure as a learning design does not mean embracing avoidable failures and lowering standards for excellence. Instead, it involves increasing the acceptability of unavoidable failures so that students are able to learn from them. Productive failure is a learning process that can be harnessed within transdisciplinary education for sustainable development to nurture underdeveloped affective competences. It is an approach that provides support for students as they experience unavoidable failures for the sake of long-term growth and learning. The course, Tackling Environmental Problems, creates conditions under which students experience the complexity of real-world problem-solving.