The purpose of this study was to better understand how Jewish day school leaders in Toronto perceive non-Orthodox Jewish day school financial sustainability. This multisite case study used a questionnaire, completed by 23 leaders of non-Orthodox Jewish day schools, and one-on-one interviews with all eight heads of school of the non-Orthodox Jewish day schools in Toronto to collect data. Both data collection instruments addressed three guiding research questions. Conclusions point toward a need to develop new ideas, to increase collaboration between the schools, and to focus efforts on raising the perceived value of Jewish day school education for prospective families.