Research on productive failure has examined the dimensions which are most beneficial for students’ learning of well-defined canonical problems in math and science. But failure plays an equally important role in solving open-ended, or ill-defined, design problems that have become prominent in many STEM-oriented maker activities. In understanding the role of failure in open-ended design tasks, we draw on Kapur’s conceptualization of productive failure and connect it to research on the role of construction in learning. We report on findings from an eight-week long workshop with 16 high school freshmen (13–15 years) who engaged in an open-ended design task with electronic textile materials. In electronic textile design tasks, a small computer, sensors, and actuators are stitched together with conductive thread to create a circuit. Our analysis focused on students’ debriefing interviews addressing two questions: (1) What range of debugging challenges do youth report encountering when creating e-textiles? and (2) How do youth draw upon the available tools and materials to generate and implement solutions to these challenges? In the discussion, we address how our findings from examining open-ended e-textiles design challenges, students’ perceptions on failure, and their resolutions contribute to the growing work on productive failure as a learning design with applicability to open-ended design tasks.