Between 1973 and 1990, Chile was ruled by Augusto Pinochet, a military dictator known for his persecution of leftists and political opponents. Although Chile transitioned to democracy, ratified the American Convention on Human Rights, and joined the Inter-American System for the protection of human rights (IAHRS) in 1990, Pinochet’s legacy of human rights abuse lingers. The Chilean military justice system exemplifies this through its ongoing jurisdiction over cases in which military personnel harmed civilians, which violates the Convention’s guarantee of access to competent courts and fair trials. This research fills a gap in the existing literature on this violation by exploring the following question: how do the combined structural weaknesses of the Chilean judiciary and IAHRS limit the Chilean military justice system’s compliance with the Convention? To address this question, I analyzed the foundational documents of the Chilean judiciary and IAHRS with a focus on how vague or inconsistent language in the articles that connect through the procedural interactions between the two institutions work together to create loopholes for the Chilean military justice system to exploit. This thesis argues that ambiguous and contradictory language in the articles of the Chilean and IAHRS documents involved in the referral of human rights petitions to the Inter-American Court limits compliance by jeopardizing the legitimacy of petitions against Chile for its military justice system’s inappropriate jurisdiction and by creating significant deterrents for those considering petitioning against Chile. Throughout the twentieth century, military dictatorships ruled several Latin American countries that have since ratified the Convention. This research could therefore illuminate tendencies central to understanding and rooting out dictatorial legacies in the region and inform more effective collaboration between the IAHRS and its Member States in addressing impunity for human rights abuse.