Although teaching is perhaps the central public activity of most university English professors, there is surprisingly little research in the specifics of expert professorial practice. Many previous studies describe, recipe-like, the end products of successful teaching, while others conflate expertise in this subject matter with pedagogical expertise. This study focuses on the moves the expert professor makes in a semester-long process of literary teaching_of a literature far removed in time and space from most undergraduates' experience_and discusses a day-to-day case study of an advanced undergraduate literature course in the writings of John Milton. By employing a 'situated learning' model explaining the incremental growth of students' knowledge and critical skills, the author details how an expert professor teaches complex works to undergraduates with no previous exposure to an author's writings. This process is generalized to describe literary learning in its particulars and the paths students must take from possessing scant knowledge about an author or historical period to their developing mastery.