Abstract In agriculture, sustainability is framed as an aspiration to achieve multiple goals including positive production, environmental and social outcomes. These aspirations include: increasing production of nutritious food; minimising risk and maximising resilience in response to climate variability, fluctuating markets and extreme weather events; minimising impacts on global warming by reducing emissions; efficiently using limited resources; minimising negative on-site and off-site impacts; preserving biodiversity on farm and in nature; and achieving positive social outcomes reflected in farmers’ incomes (revenue and profit). Here we used cropping systems simulation to assess multiple (11) sustainability indicators for 26 crop rotations to quantify their sustainability throughout Australia’s subtropical cropping zone. Results were first expressed via a series of maps quantifying the minimal environmental impacts of attributes such as N applied, N leached, runoff and GHG emissions of the 26 crop rotations while identifying the locations of the optimal rotation for each attribute. Inspection of these maps showed that different rotations were optimal, depending on both location and the attribute mapped. This observation demonstrated that an 11-way sustainability win-win across all attributes was not likely to happen anywhere in the cropping zone. However, rotations that minimised environmental impacts were often among the more profitable rotations. A more holistic visualisation of the sustainability of six contrasting sites, using sustainability polygons, confirmed that trade-offs between sustainability indicators are required and highlighted that cropping in different sites is inherently more or less sustainable, regardless of the rotations used. Given that trade-offs between the various sustainability attributes of crop rotations are unavoidable, we plotted trade-off charts to identify which rotations offer an efficient trade-off between profit and other sustainability indicators. We propose that these maps, sustainability polygons and trade-off charts can serve as boundary objects for discussions between stakeholders interested in achieving the sustainable intensification of cropping systems.