Objective indicators suggest that economic and political conditions improved in Chile between the country’s democratization in 1990 and 2011. Average incomes increased, poverty rates decreased, and the number of positive reviews of Chilean democratic institutions rose. Despite this progress, massive student-led protest waves in 2006 and 2011 demonstrated high levels of subjective discontent in Chile. This paper proposes a three-part explanation for the paradoxical emergence and escalation of the post-Pinochet-era Chilean student protests, and, in so doing, contributes to the broader understanding of social movements and political action. The first two parts of the argument relate to generational change. Firstly, a gap between expectations and capabilities provoked discontent amongst a new generation of Chilean students. Secondly, the new generation’s collective identity as “la generación sin miedo” (the fearless generation) motivated the students to turn discontent into political action. Thirdly, government and student actor agency influenced the variance in protest strength between 2005 and 2011.