This chapter analyzes the evolution experienced by Chilean society and the Chilean Armed Forces, both in their reciprocal relationship and in matters relating to the country’s national defense, from the moment of the restoration of democracy in Chile up to the present day. The conditional nature of the Chilean transition is evidenced by the 1980 Constitution, imposed by the Chilean military dictatorship, and in the prerogatives and powers reserved for the Armed Forces in that Constitution. These aspects have largely disappeared due to the advances achieved during the Chilean transition, although the aspiration for a new Constitution that would definitively end the constitutional legacy of the military government persists. The work divides the aforementioned evolution into three stages: transitional tension (1990–2000), modernizing aspiration (2000–2010), and institutional deterioration (2010 to the present). In the first stage, the civilian government sought to establish its authority over the Armed Forces, which in turn sought to preserve the power sectors and the limitations on government authority established in the 1980 Constitution, with paradigmatic examples such as the persistence of the dictator Augusto Pinochet as commander-in-chief of the Army, and the powers assigned to the National Security Council, a body dominated by the Armed Forces. In the second stage, the civilian authority achieved a significant degree of progress. This occurred through the constitutional reform of 2005 and the sanction of Law No. 20,424 Organic Law of the Ministry of Defense, and, simultaneously, under the protection of Law No. 13,196 “Copper Reserve,” a significant re-equipment and modernization of the Chilean Armed Forces also took place. In the third stage, there were significant investigations into cases of corruption in the Chilean Armed Forces regarding the purchase of military equipment. Likewise, the country’s serious social crisis (2019–2020), which led to strong repression, expressed the dissatisfaction of large sectors of the population and gave rise to a process of debate and constitutional change that has not yet been concluded. In recent years, the Armed Forces have also been involved in internal security tasks, in Araucania and on the country’s northern border. In short, in Chile during this period there have been unequivocal advances toward securing the political leadership of defense, but there is still work to be done to perfect such leadership, to achieve the full integration of the Armed Forces into society, and to establish the participation of the civil society in the design and formulation of defense policy.