Elections in many contemporary Latin American democracies unfold in a setting that complicates traditional political communication strategies. Indeed, many countries in the region are characterized by weak political parties, high levels of institutional distrust, and growing disdain for political elites. While a large body of literature has sought to explain which factors weaken parties and increase institutional distrust, less attention has been paid to the question of how these characteristics shape political communication. Drawing on the content of television advertisements created for Chile’s constitutional plebiscite campaigns, and original interviews with the creative and political teams that designed the ads, we explore how each side communicated with voters; the issues they focused on; and to what extent they relied on partisan, policy, generic, or emotional appeals. The analysis identifies important changes in messaging across the three electoral contests and probes an explanation for this variation. We find that in the absence of partisan messages, the constitutional campaigns relied first on policy-based appeals but then transitioned to generic appeals, ultimately opting for “antipolitics” messaging. These changes resulted from the expansion of the electorate and growing distrust in the constitutional convention. The analysis also underscores that pro–status quo plebiscite campaigns are more likely to deploy negative emotional language than campaigns centered on change.