This article addresses the dilemma of promoting critical pedagogy within portfolio assessment, which has been implemented in many teacher education programs to meet state and national mandates for performance-based assessment. It explores how one teacher educator works to move portfolio assessment to a level of critical self-reflection that prepares teachers to address the complex issues presented by a multicultural society. First, this article describes the ways that critical inquiry methods, democratic dialogue, and portfolio assessment can be integrated to the study of theory and preservice teachers' self-reflection as a bridge to developing a critical lens for classroom practice and a democratic society. Second, it presents preservice teachers' narratives of critical self-reflection. (Contains 3 notes.)