This paper discusses challenges and paradoxes for teaching project management (PM) in an Agile way outside of a software development context. Based on a critical analysis of two PM course iterations in a professional masters program, the paper identifies several areas with tensions between established processes, norms, values, and expectations in higher education and the Agile PM course design. Ultimately, the paper finds that fulfilling the professional masters program’s mission (to educate workforce-ready graduates for today’s Agile / hybrid working environments) would require subverting numerous norms, values, and expectations on the course design, the students’, and the lecturers’ sides. Teachers and program directors in higher education can draw on this paper’s findings to identify and manage pitfalls and paradoxes in their own PM course designs, in order to have them convey Agile PM’s principles, values, and techniques effectively while retaining a positive student experience.