Researchers have worried for decades about an “achievement gap” among students (Brantlinger, 2003; Kozol, 1991; Oakes, 1985). This paper posits that a similar and potentially widening gap is occurring in the organizations we call school systems; namely between those that learn and those that maintain the status quo. The proposition is illustrated by a qualitative case study of a school system including two years of observations of school board and curriculum meetings, public documents, personal correspondence with trustees and administrators, and informal conversations with parents. The paper draws on classical and contemporary literature of organizational learning theory (e.g., Argyris & Schön, 1978, 1996; Dixon, 1999; Weick, 1995). Organizational learning, particularly through inquiry and innovation, helps ensure the survival of systems “by helping them transform themselves from within and respond responsibly to external challenges as they exploit what they have learned in the past while exploring or innovating to deal with the present and future” (Collinson & Cook, 2007, p. 9). Balancing change and sustaining organizational learning has recently garnered considerable attention (Fullan, 2005; Hargreaves & Fink, 2006). It requires careful leadership and conditions (Collinson & Cook, 2007) that help develop organizational capacity, the “core attributes that determine the group’s or organization’s identity and determine the speed and effectiveness of members’ collective learning”—identity formation, social infrastructure, structures, and routines (Collinson, in press). The findings suggest that school systems that have maintained the status quo during the last decade or two have likely not developed the organizational capacity to close the learning gap with systems that have learned how to learn.