This paper compares the evolution of two initiatives--one in Singapore and one in New York City--designed expressly to support the development and spread of new and innovative school models. These two initiatives--Future Schools in Singapore and the iZone in New York City--reflected the hope that new school models and associated innovations could be incubated and then replicated to help create system-wide conditions that would allow new approaches to schooling to emerge. Despite dramatically different system contexts--in terms of governance, politics and professional capacity--we show how both initiatives have to deal with basic institutional, political and societal conditions that sustain conventional educational practice. We focus particularly on how common factors like capacity demands, frequent changes in policies and emerging technologies create opportunities for the development of some new resources and practices even as they reinforce many aspects of the conventional "grammar of schooling." Although this analysis emphasizes common challenges for developing more "innovative" approaches to schooling, we highlight as well the often-unanticipated developments that contribute to smaller scale innovations and incremental change.