This Research Full Paper explores different implementations of and teachers’ experiences from challenge-driven education and similar learning approaches in engineering education and other higher education contexts. Through an action research approach key concerns among the teachers and similarities and differences between the studied courses can be identified. The study highlights the potential in these learning approaches, as means for breaking and going beyond the traditional boundaries of higher education, enhancing and cross-fertilizing engineering education with other disciplines, and empowering students both as professionals and humans. It also indicates potential barriers and in-built tensions that are crucial to handle for successful implementation. The study further shows on great opportunities for mutual learning and collaboration between teachers from diverse contexts and backgrounds. The findings are discussed in relation to research within domains such as sustainability education, transformative learning, and futures studies, and opportunities for further research and development are outlined.