Informed by a systematic evidence review, this qualitative study critically examined how digital skills are developed in non-formal learning contexts. The first phase involved participant observations and interviews with organisers and facilitators of digital skills workshops in areas of different socio-economic status in Belgium, Denmark, and Italy. Preliminary findings suggest that digital skills acquisition in non-formal contexts is shaped by the format (direct instructions/free play learning), facilitation (structured/unstructured) and outcome (product- or process-oriented) of the workshops, and technological imaginaries of facilitators. Relying on participatory design techniques, the second phase involved the co-creation of interventions for digital skills practices for and with young people in non-formal learning environments. It triangulated young people’s voices (representing their practices/experiences/perceptions) with tangible design outputs (externalizing what they want/need), and with policy and educational documentation of adult stakeholders (revealing formalized processes, what should be done). Findings informed the definition of design principles.