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