What happens if we shift the focus of our teaching and learning innovations from a single classroom to an entire institution? What new kinds of questions and possibilities emerge? Can an entire college break boundaries, moving from a focus on “what teachers teach” to a focus on “what students learn?” Can we think differently about student learning if we create structures that enable thousands of students to use new media tools to examine their learning across courses, disciplines, and semesters? Bret Eynon explores these questions as he analyzes the college-wide ePortfolio initiative at LaGuardia Community College. Studying individual portfolios and focus group interviews, he also examines quantitative outcomes data on engagement and retention to better consider ePortfolio’s impact on student learning.