This qualitative, evaluative case study details the conceptual framing, development, delivery, and assessment of a privacy literacy workshop called Digital Shred. The workshop is a multi-institutional effort offered initially in-person in fall 2019 and adapted to virtual delivery in fall 2020. The conceptual framework underlying the workshop includes reputation management, behavioral surplus, data doubles, data governance, and information security damage assessments. Learning outcomes and activities were inspired by inclusive, responsive, active learning pedagogy. Anonymous formative assessment feedback suggests that participants are motivated by the personalized learning activities and value this theory-informed approach to privacy literacy.