This Element presents three case studies of interactive digital editions of Shakespeare incorporated into classroom teaching: WordPlay Shakespeare, PerformancePlus and myShakespeare. Each interactive edition combines the text of a Shakespeare play with a recorded performance. The case studies seek to understand whether and how interactive Shakespeare editions support ambitious teaching, where students are expected to engage in authentic academic tasks, experience social learning (dialogic rather than didactic), and demonstrate their new knowledge through meaningful assessments. In our time of pandemic and considerable public contention over equity and justice, ambitious teaching further requires attention to the whole selves of students – their psychological and social development as well as their intellectual attainment. This Element examines the opportunities that interactive digital editions give teachers, software developers and scholars to connect Shakespeare's works to twenty-first century students.