A partnership between The Hobbit and technology can help overcome the challenge of teaching SLA literature in the 21st century. The development of extensive reading habits is an ongoing challenge for SLA students. Tolkien wrote this work for his children in a way that helps instructors and students meet that challenge. Simple vocabulary and syntax, identifiable characters, a mythic structure at once familiar and new, and popularity that has resulted in translation into over 60 languages all combine to make The Hobbit a broadly applicable tool in SLA extensive reading instruction. This presentation illustrates the scaffolding methods, syllabus design, online journaling, AI interaction, and evaluation techniques of an upper-level CLIL literature course using the annotated version of The Hobbit as instructional material. The presentation will explore how to merge analog approaches with technologically-mediated, multi-modal study, both to enrich classroom experiences and to spark a sustainable extensive reading habit.