This article describes major but common pitfalls in teaching undergraduate students to engage in critical analysis of sport through two separate large-scale online sport sociology courses (KIN 142 and KIN 249) at the University of Illinois at Urbana-Champaign (UIUC). Three instructors at varying stages in their careers as graduate students, and one faculty member, offer first-hand reflections--autoethnographies--(Denzin, 2009, 2010) composed of personal experiences. This autoethnography provides some specific critique of the instructors' courses, reflecting on the role of the institution and the instructor as they complement and contradict each other. Each course is tuition generating and has enrolments of 750 students. Both are introductory survey courses in sports sociology; one concerns contemporary issues and the other modern society. Both courses were designed using Blackboard to be intensive--eight weeks--version of existing full semester courses. The courses incorporate multiple short reading reflections and discussion posts that ask students to reflect on their own opinions while simultaneously critically engaging with course material. Both courses utilise discussion groups to which individual graduate students are assigned as graders/markers for the entire semester. Discussion groups comprise between 25 and 30 students. Graduate students are hired as hourly workers and were assigned one discussion group per three hours of work per week (approximately), meaning a graduate student hired for 15 hours of work per week would be responsible for grading/marking five discussion groups. Topics include hegemony, socialisation and authenticity, risk, violence in relation to masculinity and culture, racial inequality and social justice, and invention and tradition in relation to social nostalgia in sport, governmentality, and "agon" (contest). The results of the autoethnographies show that many of the instructors' struggles stem from instructional design choices at various levels, some of which were in their control and some of which were decisions made by their department's leadership or other administrators at their institution. Also, teaching assistants are categorized as 'graders' and paid hourly, resulting in complicated ongoing labour negotiations at UIUC.