This article presents a microhistory of Puerto Rico that investigates the role of translation and language policy during the transition from Spanish to U.S. colonial rule. Two specific periods, namely the transitional military government from 1898 to 1900 and the first civilian government from 1900 to 1917, provide the framework within which the study is conducted. Analyses of official language and translation policies, as well as historical documents from governmental and educational contexts, illustrate the multiple, conflicting agendas employed by the new colonial power to Americanize the island. Results also demonstrate how codified policies do not fully account for the linguistic and cultural landscape in colonial contexts, thereby requiring closer examination of translation practices and beliefs and their interplay with translation policy.