Over the course of our day of multiform panel presentations, participants engaged critically with the digital as praxis, reflecting on the challenges and opportunities presented by the media technologies that evermore intensely reconfigure the social, historical, and geo-political contours of the Caribbean and its diasporas. Presenters considered the affordances and limitations of the digital with respect to a wide range of disciplines and methodologies. During our two days of discussing, exchanging, and imagining together, we picked up themes addressed in our 2014 inaugural event and, subsequently, during our 2015, 2016, and 2017 events – many of which currently feature in our first and second issues of sx archipelagos, our peer-reviewed publishing platform dedicated to Caribbean digital scholarship and scholarship of the Caribbean digital.