This chapter examines ethics in the work of L2 writing program administration in transnational higher education (TNHE). We specifically examine how the border-crossing nature of TNHE settings can give rise to conflicts of values and ethical dilemmas for administrators. In this chapter, we begin by reviewing the complex setting in which TNHE takes place and consider how navigating its institutional, political, and cultural complexities involves traversing multiple value systems. We then describe in detail two ethical dilemmas that we have experienced resulting from the complexity of the TNHE setting: the first relates to assessment and language proficiency, and the second relates to institutional policies and practices in employees’ work-life. We use these two examples to illustrate how viewing challenging administrative issues through a lens of values and ethics allows us to reflect on and adjust our own practices and cultural biases. We end the chapter by outlining three guiding principles (related to communication, representation, and transparency) that we have found can serve as a compass for taking needed action in such complex administrative contexts.