In an era of accountability, teachers must be prepared to adapt to the variability they encounter in today's classrooms. Instead of knowing only routine responses to the challenges of practice, teachers need a repertoire that is characterized by adaptive expertise. Preservice preparation can foster teacher candidates' adaptive expertise through the use of ePortfolios as web-based learning communities built upon reflection and feedback. This article reviews the literature on adaptive expertise and uses a learning-to-teach-in-community framework to explain the value of ePortfolios for supporting the development of adaptive expertise. Further, a design and evaluation plan is presented for an ePortfolio-based learning community in which special education teacher candidates practice the skills and dispositions necessary for adaptive expertise through reflection prompts that are based on real-world classroom cases and receive feedback from program faculty and practicing special educators.