Keeping humans in the loop or bringing them back into the loop in dynamically changing socio-technical or socio-hybrid systems requires the human-centered arrangement of system designs and the adoption of digital artefacts according to human capabilities and needs. When transhumanist developments increasingly propagate through society, digital sensemaking could support their co-evolution in a sensible way. We discuss sensemaking to that end, and provide a roadmap on how to integrate sensemaking processes into capacity building processes and digitalization initiatives. Cite as: Brill, D., Schnugg, C., & Stary, C. (2022). Makes Digital Sensemaking Sense?—A Roadmap for Digital Humanism in Increasingly Transhumanist Settings. New Explorations: Studies in Culture and Communication, 2(3), https://jps.library.utoronto.ca/index.php/nexj/