Solving the ‘wicked’and ‘persistent’environmental problems of the twenty-first century will require changes in the social and technological structures that guide urban development. While modern planning offers a century’s worth of solutions to environmental problems at the local scale, many of these ‘first-order’solutions exacerbate problems at larger scales (eg sprawl, auto dependency, climate change). Change of the ‘second-order’is necessary to address problems such as climate change, energy scarcity, and the destruction of finite ecosystems. The Multi-Level Perspective of Socio-Technical Systems (MLP) claims that ‘second order’structural change is resisted by socio-technical regimes—a tangle of mutually reinforcing rules, physical structures, and social networks. While regimes are critical for day-to-day functioning in a complex world, the regime structures that guide urban development in North America have resulted in human settlements that consume life-supporting resources faster than they can replenish, and result in diffuse social and environmental consequences that are difficult to ‘solve’at the local scale. According to the MLP, regimes begin to transform under the exogenous pressure of socio-technical landscape forces (eg demographic shifts, national politics, armed conflict, resource scarcity) and with alternatives incubated in socio-technical niches, or networks of actors that play by different ‘rules of the game.’