In the 20 years since the fall of the Berlin Wall, teaching post-socialist transition to undergraduate students has become increasingly challenging. This paper relates the development, planning and operation of a fieldwork module in Moscow, for Year Three geography undergraduates. It argues that "on-street" teaching and imaginative use of visual sources can partially overcome the linguistic drawbacks of fieldwork in this context. It supports the utility of fieldwork for teaching post-socialist transformation, but stresses the need for local knowledge and contacts, linguistic ability on the part of module staff, and careful planning, to overcome anticipated and unexpected challenges. (Contains 3 notes.)