The purpose of this paper is to explore the principles of Assessment for Learning (AFL) in light of John Dewey's writing about the purpose and possibility of education. In this paper, we compare Dewey's ideas to the goals of assessment for learning (AFL)--a practice emerging globally and, more locally, moved forward by the Alberta Initiative for School Improvement (AISI) program. We believe the principles behind Dewey's educational philosophy are congruent with fundamental principles of AFL. In this paper, we attempt to explicate key intersections between Dewey's teachings and AFL. We review AFL strategies and the foundational philosophy of AFL in an attempt to reveal its connection points to Dewey's educational philosophy. Specifically, we will outline seven AFL strategies and compare these to insights put forth in Dewey's work. Although there is far from adequate space to consider all the matches of Dewey's philosophy and the core principles of Assessment for Learning, we hope our quest for initial commonality might provide curriculum insight for those now working these new pedagogical activities.