Abstract: In this study we review and compare a variety of contexts for learning informed by three web-based electronic portfolios (ePs): ePortofolio, Iportfolio, and Mahara, located in University professional programs in Canada, New Zealand and Australia respectively. Our purpose is to bring to light commonalities and distinctions that emerge from three case studies drawn from interviews with three academic administrators responsible for leading the portfolio initiative at each institution. Using a complexity theory lens, we explore the eP process as an iterative cycle of learning based on self-identified forces (or events) that influence the eP's development and use. In exploration, we consider how the eP process could be understood as a complex learning system. Our question is, “What conditions inform our understanding of the eP process as a learning system?” Emerging themes include competing motivations for adoption, changing instructor/learner roles, and scaffolding for learning "events".