How does one grade an electronic portfolio? This question is one I have thought about, have enacted, and have written about, primarily in reference to ePortfolios used in writing classrooms (Yancey, McElroy, & Powers, 2013). But what happens when the content and developmental levels are changed, in this case from an undergraduate first-year writing class to another required class, this one offered at the graduate level, Digital Revolution and Convergence Culture? Is using a scoring guide, the preferred approach in writing classes, the best approach in this new context? Or, following Moss, Girard, and Haniford (2006), could one use outcomes to "stage a conversation" around a student's ePortfolio; if so, what might a staged conversation look like? Or what might happen if instead of using outcomes as a framework, students themselves set the terms for that conversation? Here, I consider these options, attending especially to the importance of making good judgments and of fostering learning.