Part of the Volume on Civic Life Online: Learning How Digital Media Can Engage Youth. Youth today are often criticized for their lack of civic participation and involvement in political life. Technology has been blamed, amongst many other causes, for fostering social isolation and youth's retreat into a private world disconnected from their communities. However, current research is beginning to indicate that these might be inaccurate perceptions. The Internet has provided new opportunities to create communities that extend beyond geographic boundaries, to engage in civic and volunteering activities across local and national frontiers, to learn about political life, and to experience the challenges of democratic participation. How do we leverage youth's interest in new technologies by developing technology-based educational programs to promote civic engagement? This chapter explores this question by proposing socio-technical design elements to be considered when developing technology-rich experiences. It presents a typology to guide the design of Internet-based interventions, taking into account both the affordances of the technology and the educational approach to the use of the technology. It also presents a pilot experience in a northeastern university that offered a pre-orientation program in which incoming freshman designed a three-dimensional virtual campus of the future and developed new policies and programs to strengthen the relationship between college campus and neighbor communities.