How can students demonstrate that they are meeting standards while showing who they are as individuals? In 1992, the Exhibitions Project at CES led the first-ever research project on digital portfolios. Technology has changed dramatically in the ensuing quarter-century, but the essential questions for creating digital portfolios have endured. Participants will address these essential questions including, "Assessment: How do we determine what's 'good'?" to "How do the portfolios become a valued and valuable part of school life?" We will hear about how University Heights High School (Bronx, NY) addressed these questions in the original study and see samples of current students' Richer Picture digital portfolios. In addition, participants will engage in a calibration protocol for reviewing student work, using online rubrics and narrative assessments.