Most of the prior research concerning instructional design (ID) education has taken place in the context of introductory courses. However, teaching advanced ID students differs from teaching novices because advanced students are capable of independent action, but also still need some targeted instruction to develop their own design skills and identities. To increase understanding of advanced ID education, we conducted this collaborative autoethnography of teaching advanced ID courses. Through autoethnographic reflections from two advanced ID instructors, supplemented by interviews conducted by a third researcher, and jointly analyzed by our research team, we studied some of the work involved in teaching advanced ID students. We identified three themes through our study. Advanced ID instructors: (a) helped students reflect on design; (b) helped students recognize and adapt to design challenges; and (c) balanced direct instruction with guidance and coaching. We conclude by discussing implications of our findings for other advanced ID educators.