The convergence of innovations in digital technologies and expanding global internet connectivity has given rise to an emerging field of study identified as Digital Media and Learning (DML). (Davidson and Goldberg, 2009; Gee, 2009; Ito, Horst and Bittanti, 2008; Jenkins and Purushotma, 2008). In describing his work for the MacArthur Foundation's Digital Median and Learning Initiative, Gee (2009) argues the field of digital media and learning is in its infancy. Gee contests there is an urgent need for scholars, with interest in various aspects of digital media, to develop studies that contribute to a body of knowledge about how digital technology may enhance learning and, potentially, transform society. This study was developed to make such a contribution. Although the literature on digital portfolios places great emphasis on the portfolio as a tool to support student learning, few studies include students' voices and offer thick descriptions of their experiences related to creating and using digital portfolios, nor how those experiences may enhance learning. In response to this deficit, this qualitative case study gives voice to 27 high school seniors and 7 senior class teachers from a Southern California high school that has created a technology rich culture, where, for the past ten years, all students in grades 9-12, and all teachers are required to create and maintain an internet based digital portfolio. This investigation illuminates the potential of digital portfolios to support learning by highlighting the successes and shortcomings of the institution's current digital portfolio practices as directly expressed by students and teachers. The study offers further insight into possible connections between digital portfolios and learning by giving voice to insights offered by students and faculty regarding possible new learning strategies enhanced and enabled through emerging types of digital media applications such as social networking sites, blogging and text messaging. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]