This article reflects on two specific sets of questions—both of which were prominent in conversations regarding the future of teaching in higher education—that emerged as we developed a pedagogy designed to advance the primary substantive goals of environmental justice. The first set of questions asks how to enhance interdisciplinary thinking and communication in a single course; the second asks how best to teach critical thinking online. We identify key challenges in both areas in a discussion of our experience in teaching two contemporaneous venues—one on-campus and one online—of an environmental justice course grounded in the subfield of political theory.