The Dujiangyan irrigation system, China’s largest, is one of the world’s most important examples of sustainable agropolitan development, maintained by a relatively decentralised system of governance that minimises bureaucratic oversight and depends on significant local autonomy at many scales down to the household. At its historic core in the Chengdu Plain, the system has supported over 2000 years of near-continuously stable urban culture, as well as some of the world’s highest sustained long-term per-hectare productivity and diversity of grain and other crops, especially considering its high population density, forest cover, general biodiversity and flood management success. During the past decade, rapid urban expansion has turned the Chengdu Plain from a net grain exporter into a grain importer, and has radically transformed its productive functioning and distinctive scattered settlement pattern, reorganising much of the landscape into larger, corporately-managed farms, and more concentrated and infrastructure-intensive settlements of non-farming as well as farming households. Community-scale case studies of spatial-morphological and household socio-economic variants on the regional trend help to articulate what is at stake. Neither market-driven ‘laissez-faire’ rural development nor local state-driven spatial settlement consolidation and corporatisation of production seem to correlate well with important factors of resilience: landscape heterogeneity; crop diversity and food production; permaculture; and flexibility in household independence and choice of livelihood. Management of the irrigation system should be linked to community-based agricultural landscape preservation and productive dwelling, as sources of adaptive capacity crucial to the social-ecological resilience of the city-region, the nation and perhaps all humanity.