Policy and practices of quality assurance in higher education have followed a progressive development path in Chile. However, after a crisis that undermined trust among stakeholders, over the last decade demands for major reforms have increasingly constrained the governmental agenda. Following national and international reviews involving virtually every actor in the system, boosted by a context of weakened legitimacy, Chile is now on the verge of a new wave of reform in the area. Under an evolutionary perspective on quality assurance, it is believed that the current policy stage entails an opportunity for the system to evolve to higher thresholds of complexity by means of building on a much more mature and consolidated arrangement. Aiming to explore the consistency levels between the identified quality assurance challenges and the policy actions, the chapter suggests criteria for assessing both processes using a ten-dimensional scheme based upon key features of a quality assurance framework. By bringing together the dimensional analysis and the evolutionary perspective, obstacles are identified which are preventing the current system from reaching those higher levels of complexity.