This essay captures one instructor's experience implementing, revising and re-implementing ePortfolio practices over several years at LaGuardia Community College, CUNY. It outlines and analyzes the strategies that have worked best in rendering more visible the learning process to students generally inexperienced in academic pursuits, namely (1) determining "learning" as the primary purpose of student ePortfolios, (2) helping students discover the language to talk about the learning process, (3) providing continual guidance to enforce critical and academic analysis, and (4) celebrating technological advances that have enhanced pedagogical changes. This process of experiment, failure, reflection, and success should be of interest to teachers and scholars concerned with using technology to empower learning among nontraditional students new to the college environment.