Electronic portfolios (eportfolios) can increase reflection, develop content and pedagogy skills and facilitate communication between teachers and administrators. However, they have limitations. Despite resources that teacher institutions devote to eportfolios, research suggests that most implementations are of limited duration. In a climate where sustained professional development and lifelong learning are necessary to remain competitive, organizations should reevaluate how eportfolios are implemented to sustain use and maintain skills deemed important by teaching organizations. Using principles of change theory, this article identifies several eportfolio challenges and how they may be improved through principles of personal learning environments. Implementation procedures and limitations are also provided.