For students to thrive and achieve at high levels, they must be interested and emotionally invested in their learning. Why? Because motivation, or the desire that propels one to do something, leads to engagement, where students are being attentive to their tasks, putting forth positive effort, persisting through challenges, and advancing their ideas and understandings with a sense of intention. While classroom environment and teacher-student relationships influence motivation and engagement, these areas cannot be fully captured in a stand-alone assignment. Educators can, however, look at both the content and the design features of an assignment. These two areas serve as close proxies for student engagement because they hold the potential to ignite and propel interest and enthusiasm. In this brief, the authors take a closer look at the criteria for motivation and engagement in rigorous assignments, specifically the role of choice and relevancy. What does it mean for educators to offer their students authentic choices? How can educators bring relevancy to their assignments, and what do they need to be cautious about? And finally, what steps do educators and school, district, and state leaders need to take to ensure that more students benefit from engaging learning opportunities and the successful outcomes that follow?