Paulo Freire, bell hooks, and Ira Shor have been criticized as theorists not concerned with the institutional realities of American education (e.g., grades and standardized exams). This paper argues that these teacher-researchers speak to the issues encountered in developing electronic portfolios in high schools and colleges. The imposition of high-stakes assessments from outside of the classroom (often legislated by state governments and enforced by state departments of education) creates environments where concerned teachers must teach toward the tests. Yet in classrooms where computer-mediated writing occupies a good deal of the students' time, more and more teachers and researchers are finding that student creativity and risk-taking do not directly correspond to standardized assessment. The most recent advances in electronic portfolio assessment, however, demonstrate that communication-based writing evaluation can be developed not only in individual classrooms, but also across university writing programs or throughout state education systems. This paper briefly sketches the practices developing in electronic portfolio systems and shows how these methods of assessment address concerns about validity and how they change the tenor of the conversation when discussing reliability. Drawing on Brian Huot's ideas in "Toward a New Theory of Writing Assessment," the paper suggests that electronic portfolio assessment can both reinvigorate critical pedagogy and can benefit by addressing the challenges raised by Freire, hooks and Shor. Contains 20 references. (Author/RS)