DescriptionThe flipped classroom method of instruction involves a shift in how learning and teaching take place. Students in a flipped classroom access video tutorials at home as their primary means of instruction, while they work on rich problems requiring procedural and conceptual knowledge in class. The flipped classroom approach has been gaining popularity in higher education (Abeysekera & Dawson, 2015) and in mathematics (Muir & Geiger, 2015). Although studies have addressed differences between flipped and traditional methods of instruction, few have closely examined how to design activities in a flipped classroom that develop students’ higher-order thinking skills (O’Flaherty & Phillips, 2015; Song & Kapur, 2017). Kapur’s (2008) theory of productive failure states when students have an opportunity to generate and explore solutions to a challenging task prior to being instructed on it, they are better positioned to consolidate their knowledge during and after instruction. The purpose of this mixed methods study was to determine whether repurposing the flipped classroom to include productive failure results in students’ improved understanding of targeted mathematical content. Through work samples and a survey, it was determined that there was no statistical significance between groups in terms of students’ performance on course assessments and video-watching behaviors. Correlations among various course assessments revealed a significant correlation between students’ work on one productive failure invention task and its corresponding conceptual knowledge posttest item. Through video footage of in-class problem solving and a focus-group interview, qualitative information about students’ knowledge development helped explain differences between the two learning environments. Students who had the productive failure experience described their peers as critical to their learning, whereas students who did not described their instructor as critical to their learning. A detailed look at individual groups in the productive failure condition revealed that students who generated more solutions and had routines for working in a small group on the invention tasks each week realized greater success, as evidenced by work samples and posttest items. The results of this study will be used to guide the design of undergraduate mathematics flipped classrooms so that online and in-person class activities promote deep conceptual understanding.