The Arab uprisings and the related wave of protests across the globe over the past few years have spurred a revisiting of explanations of protests. Moreover, attempts to reconcile structural conditions with contextual factors animate these debates. In investigating the role of structural factors in causing anti-government protests – namely burgeoning young population and the penetration of information communication technology (ICT) – we attempt to bridge these debates through a mixed method of analysis. At the global level we employ a cross-national, time series analysis between the years 1995 and 2011 to investigate the role and interaction of youth bulges and ICT in explaining the onset and diffusion of anti-government demonstrations. We find that rising numbers of young people who are increasingly connected through information communication technology increase the diffusion of protests. In other words, when the enhanced technological means of protest are fused with the grievance and opportunity-based structural conditions often witnessed in countries with large youth bulges, the proliferation of anti-government demonstrations is multiplicatively heightened. A nuance in our results, however, suggests that it is the proliferation of technology that is more important in explaining protest diffusion. In contrast, we do not find that either of our variables of interest affects the probability of the outbreak of protests. In our global analysis, however, we are unable to do anything more than control for political sources of grievance. In order to demonstrate the significance and impact of these more contextual factors we turn our attention to specific cases from the Middle East from 1995 through 2011– most notably Algeria, Egypt, Iran, and Tunisia. We first analyze the degree of fit of the global model to the specific case. Next, we discuss this variance in terms of national and regional contextual factors and history through a qualitative linkage of socio-political context to the situation of youth populations and ICT in that country that has led to its particular outbreak and persistence of protests. In this manner we seek to highlight the means, motives and opportunities of anti-government demonstrations globally and in regards to the specifics of the Middle East.