The “Arab Spring”, a revolutionary wave of demonstrations and mass protests that began on 18 December 2010, put over 20 countries into political turmoil and has caused major political changes in the Arab world. The occurrence of these events surprised in scale and scope many Western observers; international democracy promoters struggled hard to find adequate answers to this suddenly popped up window of opportunity for regime change. However, their influence seems to be rather mixed: to date, only four Arab countries, namely Tunisia, Egypt, Libya, and Yemen, managed to force rulers from power, still without a guarantee that democracy will survive. Even worse, in some cases such as Syria the international community could not prevent the escalation of violence to the scale of war. It is time to rethink the international democracy promotion toolbox and critically examine its effectiveness in times of political crisis. As a first step, this paper assesses and compares how democracy promoters reacted to the Arab spring in the different countries affected and how they interacted with governments and representatives of the protest movements in order to influence the direction of regime change. Based on a middle-n qualitative comparison, it will be argued that the international democracy promotion community used a wide array of democracy promotion tools, but without systematically assessing context and timing. That is way it largely failed to effectively engage in the critical juncture of the Arab spring.