This study explores the factors that shape students’ experience with instructional choices in classroom-based settings, and the role of instructional choice design in positively influencing student engagement and the development of self-regulation skills among high school students who attend an urban high school in the Mid-Atlantic Region, referred to as Aspiration High School. A range of cultural, structural and human resource factors are found to have a limiting effect on students’ experience with quality instructional choices in school, and as a result, limits their opportunities to practice and develop the self-regulation skills necessary for navigating choices at levels of complexity that mirror the world beyond school (Winne & Perry, 2000; Winne & Hadwin, 1998; Winne, 2001). Teachers and students of Aspiration High School were surveyed to gather insights on their experiences of and perceptions on choice in learning. Two teachers engaged in a series of collaborative lesson design cycles that involved choice-based lesson design, implementation with observation, lesson debriefs, and student work analysis, as well as pre and post student interviews and focus groups. This study identified five elements of high-quality choice designs, and argues for quality choice design as an important mechanism for cultivating learner engagement (Katz & Assor, 2007), developing interventions to support self-regulatory skill development among learners, and nurturing pedagogical shifts among teachers toward more learner-centered designs and practices.