The following study looks into a twenty-five year political cycle of democracy in Chile (1989–2017). It describes the performance of political and economic institutions in transition times (1989–2013) and their ability to adapt to challenges in post-transition (2014–2017). Challenges involve macro-level constraints (end of the super commodity cycle) and micro-level pressures (protests and mobilizations). This article concludes that moderate, gradualist reforms in twenty-five years continue to be viable options to secure growth and governance, but in light of social demands and economic slowdown, institutions are exhibiting difficulties in reaching new accords. Difficulties relate to the persistent nature of neoliberal conservatism, macroeconomic constraints, and local structural heterogeneity.