On January 15-16, 2018, the School of Collective Communication Sciences of the University of Costa Rica, in collaboration with the Institute of Communication and Image of the University of Chile, Faro Digital Argentina, the Berkman Klein Center for Internet & Society at Harvard University, and UNICEF, co-hosted the third regional Symposium “Conectados al Sur: Costa Rica” on digital transformation and new challenges for the inclusion of youth at the Omar Dengo Foundation in San José, Costa Rica. Building on the second regional symposium “Conectados al Sur: Chile,” the event aimed to analyze the state of research, development, political activity, and progress around youth and digital media to promote the inclusion and participation of children and young people online, and serve as a space for the exchange of ideas and initiatives to encourage collaboration among participants across regions and continents. The symposium focused on three interconnected topic areas: artificial intelligence (AI) and emerging technologies, digital citizenship, and the digital economy. In addition to these three thematic axes, the event explored new research and development methodologies that seek to encourage youth participation and inclusion online, including 1) co-design with young people, 2) participatory research, and 3) the construction of narratives, digital media content, and information visualization. To capture and include youth voices, the event incorporated learnings from the Conectados al Sur Latin American workshops that were hosted in five countries prior to the symposium. The workshops examined young people’s ideas, attitudes, and perceptions around the three focus areas noted above (artificial intelligence (AI) and emerging technologies, digital citizenship, and the digital economy).