Although engineering education has been practiced at the undergraduate level for over a century, only fairly recently has the field broadened to include the elementary level; the pre-college division of the American Society of Engineering Education was established in 2003. As a result, while recent education standards require engineering in elementary schools, current studies are still filling in basic research on how best to design and implement elementary engineering activities. One area in need of investigation is how students engage with physical failure in design tasks. In this dissertation, I explore how upper elementary students engage in failure-prone engineering design tasks in an out-of-school environment. In a series of three empirical case studies, I look closely at how students evaluate failed tests and decide on changes to their design constructions, how their reasoning evolves as they repeatedly encounter physical failure, and how students and facilitators co-construct testing norms where repetitive failure is manageable. I also briefly investigate how students' engagement differs in a task that features near-immediate success. By closely examining student groups' discourse and their interactions with their design constructions, I found that these students: are able to engage in iteration and see failure-as-feedback with minimal externally-imposed structure; seem to be designing in a more sophisticated manner, attending to multiple causal factors, after experiencing repetitive failure; and are able to manage the stress and frustration of repetitive failure, provided the co-constructed testing norms of the workshop environment are supportive of failure management. These results have both pedagogical implications, in terms of how to create and facilitate design tasks, and methodological implications--namely, I highlight the particular insights afforded by a case study approach for analyzing engagement in design tasks. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]