Despite the growing scholarship on investigative journalism in Latin America, very few studies have addressed collaboration across newsrooms in the region. By analyzing the responses of 251 journalists who work for investigative units in Latin American news outlets, this study explores a) the reasons why Latin American journalists are increasingly seeking to participate in national and transnational collaborative enterprises, b) the challenges they identify, and c) the role digital technologies are playing in this trend of transnational collaboration. Using mixed methods, we found that collaborations occur to enhance the impact of investigative projects, to reach larger audiences, and to achieve a big-picture coverage. We also found that safety is an important motivation to work in conjunction with other newsrooms-by collaborating, journalists are able to strengthen security measures and challenge censorship. Yet, coordinating teams-especially at the transnational level-remains the biggest challenge to overcome. Digital technologies are significantly related to reporters' likelihood of collaborating, but these technologies require other reporting skills to be useful for investigative journalism. Implications for research and practice are discussed.