Research on authentic learning has been predominantly focussed on skills-based training: there is a paucity of research on models of authentic learning available for adaptation in the humanities undergraduate classroom. In this article, I will seek to address this gap by proposing that legal trials are ideal models for designing authentic learning scenarios in undergraduate teaching and learning contexts, with a specific focus on the humanities. First, I discuss why and how the structure of legal trials can produce authentic learning environments. Second, I present an undergraduate classroom project that combined two disciplinary fields -- Shakespearean drama and criminal law -- in an effort to enhance student learning and engagement. I outline how the authentic learning scenario (ALS) was implemented and evaluated and, finally, reflect on the barriers, challenges and potentially transformative effect of authentic learning environments on students and educators. This new intervention combines legal studies and English literature in order to create authentic learning environments to increase interactions amongst students, enhance students' learning, and foster conditions for transformative learning.