Bridging the digital divide is a major endeavour in many cities, especially offering learning opportunities for underserved groups. As a major target group, teenagers are addressed. While the first stage was to provide access to technology, empirical research has shown that support is necessary to develop the necessary digital literacy. But as we will show, only full integration into the life world of teenagers will really support their learning process. Using examples from our fieldwork in a regional learning environment, we focus on schools and youth centres as being very important locations for the personal development teenagers. Through a careful analysis of strengths and weaknesses especially of the so-called Web.Punkte projects, we will suggest further activities to reach the next stage of life world integration.