With the rise of so-called fake news as a global phenomenon, interest in propaganda analysis has advanced along with the recognition of the fundamentally social process of interpretation. In this essay, we explore the use of cross-national dialogue among German and American undergraduate students who are seeking to better understand how media messages are interpreted and how they inform and guide the civic actions of citizens. We describe and analyze five lessons that used a virtual exchange comprised of a variety of digital media platforms, texts, and technologies to support the cross-national study of contemporary propaganda. We observed that cross-national dialogue enables students to gain sensitivity to the role of cultural context in interpreting propaganda. Rather than conceptualize propaganda education as an ideologically benign set of context-free skills, pedagogies that include opportunities for cross-national dialogue foreground the importance of cultural specificity as a means to unpack the complex discursive context of propaganda as digital political communication.