This article examines the main contributions of five open-access primary resources digitization projects that have been created to support the study of Latin America and the Caribbean as part of a collaboration between institutions in the United States, Latin America, and the Caribbean: the AHPN: Archivo Digital del Archivo Histórico de la Policía Nacional de Guatemala; Brasil: Nunca Mais digit@l; Archivo Mesoamericano; Digital Archive of Latin American and Caribbean Ephemera, and the Digital Library of the Caribbean (dLOC). The article provides an overview of each project, describing not only the unique contents that have been preserved and made freely accessible via the Internet, but also the innovations and novel contributions introduced by these projects in various realms. We close the article with a discussion of lessons learned in how to undertake and manage digitization projects, address ongoing challenges, and consider future directions for these kinds of initiatives.