Iteration and improvement are important attributes of design, tacitly indicating that failure is also a part of the process. There are different conceptions of failure in engineering contexts than in other academic settings. Therefore, for beginning designers, these failure experiences may be perceived as mishaps, lowering confidence or interest. Given the seeming disconnect between the nature of design and the goal to foster design identities, it is important to understand experiences of failure and key elements in making failure a learning experience while designing. To map, assess, and synthesize findings related to failure experiences, a systematized literature review was conducted using the EBSCO Education Source database and conference proceedings from the American Society of Engineering Education and IEEE Frontiers in Education annual conferences. Search terms included variants of "failure" and STEM or design education. Thirty-five articles were identified with primary source investigations of failure in the classroom and included in the thematic synthesis. Key findings highlight varied interpretations of failure, even in design, student reactions to failure experiences, failure as a mechanism to uncover key concepts and promote reflection, and the importance of a safe climate for encountering failure.