In many engineering sectors, cycles of prototyping have shortened because of new technological advancements and more pressing urgencies to be innovative. As a consequence, important skills and attitudes that were traditionally learned on the job have now become a responsibility of institutes of higher education. Universities are not only expected to develop students to be industry-ready when they graduate, but they must assure they are innovation-ready as well. One way of doing so is to make students innovate on a more regular basis and by making them more comfortable with learning from the failures arising out of such shortened cycles of innovation. Learning from failure is well studied and established in some areas of education, such as the ‘Productive Failure’ approach in the domain of mathematics. However, lessons learned from such contexts may not immediately apply to the engineering context. By comparing a one semester Design Thinking and Innovation Course with a one-week cross-cultural design thinking workshop at an engineering university in Singapore, this study aims to find out how learning from failure is manifested to engineering students. The study, in drawing on observations, interview data, and students’ reflections provides several insights, such as identifying different types of failures that students encounter in their design work and highlighting two core issues (teamwork and grades) that may facilitate or hamper the extent to which students are willing to innovate. This paper gives pedagogical suggestions on how design and innovation can be taught to engineering students, specifically by taking the perspective of learning from failure and its relationship with innovation into account. This paper thus addresses the CDIO Standards 5 and 7.