Teaching in the online classroom is becoming commonplace for instructors as universities seek to grow enrollments and tap into unexplored markets. Many instructors, however, are often unprepared for the nuances of distance education and apprehensive about making the transition to online learning. This article aims to discuss common challenges for instructors of high-enrollment online courses (70+ students). Course design and instructional effectiveness are some of the most significant challenges facing instructors tasked with managing large online courses and those challenges align with the areas students commonly consider as necessary for successful online delivery. Using examples from large online classes and the existing research on best practices in online education, ways to minimize those challenges will be discussed. These suggestions include recommendations for assignment construction, including the use of group work, collaborative assignments, e-portfolios, as well as for planning course design, including consistent deadlines and course structure. These suggestions are aimed at mitigating student and instructor frustration with high enrollment online classes.