This article chronicles the development of a portfolio system used primarily to assess special education high school students on a variety of traditional and non-traditional standards and skills. Developing, capturing, sharing, and assessing student learning can be problematic when traditional testing or classroom assessment methods are not an option. Digital portfolios, when integrated correctly, provide meaningful opportunities to capture authentic student learning and assess students' growth. Additionally, digital portfolios can show evidence of student progress and allow students to participate in the assessment process, as well as facilitate opportunities for parents (and future teachers or organizations) to observe and support a child's work. We describe the development, implementation, and evaluation of a digital portfolio pilot program in a special education high school. The pilot was created in response to the need for opportunities to assess authentic student work through a variety of multimedia formats, intended to travel with students as they advance through the school system and beyond. As a result of the data and experiences, it is recommended that integrating digital portfolios into the teaching, reflection, and assessment processes when working with students with disabilities, is a way to increase opportunities for authentic assessment of traditional and non-traditional content areas, increase technology integration in classroom and community settings, and as a means to support and capture project-based learning.