Imagine 120 students sharing 5 computers, yet feeling that they are part of an interconnected world. This is the social context framing digital learning for African art students, the material limitations and cultural imaginations of which this chapter is concerned with. Based on extensive ethnographic engagements at TaSUBa, a national institute for arts and culture in Tanzania, this chapter investigates the development of digital media skills. Using the concept of digital learning to cover the acquisition of ICT skills as well as the use of ICT as a learning tool, the analysis spans from early expectations of connectivity to current forms of media engagement. Focusing on the social and cultural aspects of digital learning, the concept hybrid media engagement is introduced to capture the creative ways in which African art students overcome limitations in infrastructure, while exploring new forms of cultural production.