Educators have long recognized that students gain important skills through real-world learning, which frequently takes place outside school hours or school walls. In Boston and Providence, after-school program leaders engaged in a bold experiment to formally recognize these skills through an innovative credential called a digital badge. For two years, the Rennie Center followed teams in Boston and Providence as they created a digital badging infrastructure and measurement system. This report shares successes and lessons learned from this effort, providing guidance for student-serving organizations exploring opportunities to support and acknowledge students' non-academic skills.