Online teaching and learning has been adopted throughout higher education with minimal critical attention to the challenges it poses to traditional definitions of academic labor. This chapter explores four areas where the nature of academic labor becomes contestable through the introduction of online instruction: (1) the boundaries demarcating work from personal time; (2) the relative invisibility of online labor; (3) the documentation, recognition, and rewards attendant to online instruction; and (4) the illusory empowerment of online students as consumers. The theory and practice of what constitutes “legitimate” labor in higher education require substantial reconsideration to incorporate the online dimension.