While it is commonly accepted that being a reflective practitioner is important, teaching students how to do this is less often addressed. As part of larger curricular revisions, Parsons School of Design made the decision to embed the use of an online learning portfolio (LP) at the core of the first-year experience. The addition of the LP was intended to be an integral component in supporting students as they develop the reflective skills of discovering themes and patterns in their own work, analyzing their experiences, and making connections across courses and contexts. Curricular shifts emphasized reflection on the process of making in order to foreground "thinking" embedded in practice. This article chronicles a two-year pilot in which we tested strategies and refined assignment prompts using the LP, looking at both the student work and faculty development that paralleled the adoption of the LP.