Classroom drama holds promise for student learning across disciplines. When Shakespeare's works are included in diverse classrooms, supported by drama activities, students can embody, voice, and explore themes and societal issues, bringing such themes alive. This study documents challenges and opportunities reported by teachers in their first-year teaching as they participated in an innovative cross-national partnership between Globe Education, Shakespeare's Globe, London and the School of Education, University of California, Davis. Survey results found new teachers' value exceeded their self-confidence in implementing Shakespeare and drama-based practices in their teaching. Teachers managed to infuse drama activities in classrooms, conducted inquiry into students' responses, and reported the need for further preparation to enact program practices. Two vignettes of classroom work further illustrate challenges and possibilities of partnership practices, and highlight needed adaptive work for successfully incorporating drama and Shakespeare in classrooms to explore social, cultural, and historical conflicts, themes, and dilemmas.