In the late 1980s Czechoslovakia was considered one of the most repressive countries in Eastern Europe and a staunch Soviet ally. In the aftermath of the ‘Prague Spring’ of 1968, repressed with Soviet help, the regime managed to remove virtually all expressions of dissent. Yet in the fall of 1989 civil society forces inspired a popular uprising that put an end to Czechoslovakian authoritarianism and ushered in the transition to democracy. How could a ‘Velvet Revolution’ from below take place in such a repressive context? What role did civil society actors play in the transition? And what structural and international factors help us solve this puzzle? These are some of the questions this working paper seeks to answer.