The current shift in U.S. educational reform toward standards and guiding frameworks that are more inclusive of twenty-first-century competencies has created a need for research regarding the assessment of these skills. Also, needing further exploration is an understanding of how these new learner-centered assessments may impact students. Partnership for 21st Century Learning (2006) developed a framework that encourages educators and policy makers to create curriculum that provides for more rigorous cognitive endeavors such as, critical thinking, problem-solving and reflection. Educators must then understand how acquisition of these skills impacts learning and learners. Digital portfolios allow students to create individualized expressions of their learning (Barrett, 2007). The current research lacks a discussion of how the digital portfolio creation process may impact students. This study addresses this gap in the research. Over the last 10 years, educators have begun to utilize digital portfolios, as a means to, assess cognitive processes such as those promoted in the Partnership for 21st Century Learning framework (2006). This study reports on a specific case that may aid educators in understanding the student experience as it relates to metacognitive skills when developing and utilizing portfolios as a learning tool in an early childhood program. Using the seminal metacognition work of John H. Flavell as a foundation, this study hopes to capture the developing metacognition of three to five year olds as they develop digital portfolios. [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.]