This chapter explores the context, challenges and priorities for designing a robust, school-based, next-generation assessment system-one with the power to enable learning in a networked, digital world. The next-generation assessment envisaged here does not run counter to any national or state-based assessment system. Nor does it seek to compete with those next-generation, highly technologized assessment instruments developed by multinational business and educational partnerships. Rather, this next-generation assessment is envisioned as a complementary assessment system suited to the unique profile of individual schools, developed by those particular communities, with modest funding. It positions schools as catalysts for extending their networks of mentors and partners in purposeful, inclusive yet accountable ways. Central to its design is the desire to engage and channel young people towards their best performances and future potential, while building their social and civic consciences as tomorrow's citizens. To this end, we identify essential learnings for effectively navigating those interconnected spaces inhabited by young people, superimpose an axis of assessment options and propose an interweaving with relational and communication cables, or purposeful connections. We offer suggestions for design priorities for next-generation assessment.