Educators are regularly confronted with moral dilemmas for which there are no easy solutions. Increasing course sizes and program enrolments, coupled with a new consumerist attitude towards education, have only further exacerbated the quantity and quality of students' requests for special academic consideration (Macfarlane, 2004). Extensions, late submissions, and grade bumps--once rare--are now commonplace. However, there is very little in the pedagogical literature that addresses these everyday dilemmas. In a culture of transparency, unspoken policies that address these requests are the form of learner consideration that is the least transparent to students and educators alike. Here we explore some of the variables that contribute to the complexity of these dilemmas, and the ethical ideologies that can inform their resolution. Our goal is not to provide best practices, but rather to facilitate reflection about how individuals make these decisions. The idiosyncratic nature of these decisions can be framed as a reflection of different ethical ideologies, and we describe one approach to framing individual ethical ideologies from the business literature. Finally, we consider whether faculty should be making these decisions at all, using the centralization of academic integrity (cf. Neufeld & Dianda, 2007) as a model, and explore its parallels with issues around ethical dilemmas in teaching.