As portfolios gain currency as an assessment alternative to report cards and transcripts, many schools are beginning to use them to get a more accurate idea of students' capabilities. The Exhibitions Project at the Coalition of Essential Schools (Brown University) is developing a way to address problems associated with large-scale use of portfolios. The Digital Portfolio is a computer-based tool for what the Project terms "planning backwards," or considering what a graduate should know and how the school can arrange its system to inform the graduate. The Digital Portfolio is a hypermedia document students can use to construct a portfolio by filling computerized "folders" of stated goals and establishing a longitudinal record of student achievement. The Digital Portfolio is being pilot tested in Eastern High School, Jefferson County (Kentucky) and Thayer High School, Winchester (New Hampshire). At Eastern High School, members of the senior class are putting portfolios together, but at Thayer the portfolio protocol has been articulated for the entire school. Work at these two schools is helping define some of the issues of implementing the Digital Portfolio, including the time and space requirements to put them together and the technical requirements for maintaining them. (Contains 11 figures.) (SLD)