The Napoleonic invasion to the Iberian Peninsula provoked a crisis of political legitimacy in Chile's main cities and provinces. What it began as an autonomist revolution eventually led to a civil war with separatist aspirations. This article examines this context of revolutionary civil war in a key period of Chilean history: Bernardo O'Higgins' government (1817-1823). In order to accomplish this, the article analyses the reports and letters prepared by five US agents living in the country during the o'higginista administration. They show important aspects of Chilean factionalism, and the involvement of North Americans in disputes between the so-called Logia Lautaro and the group led by Jose Miguel Carrera. They also give an idea of negotiations led by O'Higgins to achieve the recognition of Chilean independence from the United States, and the value assigned to discussions around both republican and monarchical regimes by the Chilean elites.