This article explores the often-ignored role of "middlemen" in the mass actions that surrounded the fall of communist governments in 1989/90 and the Color Revolutions in post-Soviet space in the early 21st century. These individuals had ties to both sides and the capacity to use the media to disseminate information about the challenge to authoritarian power. Looking at the Leipzig demonstrations in the GDR, the Georgian Rose Revolution, and the Solidarity movement in Poland, this article argues that middlemen made the crucial difference between successful mass protests and failed ones, serving as a back channel for communication between regime and opposition.