Virtual schooling is expanding as an alternative to traditional public schooling in the early twenty-first century. This paper analyzes virtual schooling with regards to the democratic associational aims of public schooling as conceived by John Dewey. We examine the general landscape of virtual schooling by looking at recent history, governance, and student performance in these schools. Next, we analyze the significant ways in which virtual schools fail to meet associational aims for schooling. We conclude with a normative argument about the nature of new educational trends and innovations, drawing from Dewey's ideas in The School and Society to articulate the importance of aligning those innovations with democratic social ideals.