Delta ecosystems are vulnerable to climate change from rising temperatures and altered rainfall patterns, as well as further threats from salinity and erosion due to coastline exposure. Smallholder farmers in deltas are adapting to these risks through cropping systems intensification and diversification, but it is unclear which cropping options offer better profitability and less risk and what transformational support is needed. Using qualitative and quantitative primary field data from southwest coastal Bangladesh, this research analysed risk perceptions and adaptation responses and evaluated the profitability of seven cropping systems. Rainfall anomalies, extreme weather events, and seasonal price fluctuations were core risks for farmers. Risk management strategies included adjusting sowing/transplanting dates, changing crop cultivars, increasing chemical applications, storing irrigation water, and seeking market updates. The dominant systems (rice/rice/fallow, rice/fallow/fallow) had the lowest profitability, while systems with vegetables had the highest profitability. The risk analysis estimated that the dominant systems would incur losses every three years and rice/watermelon/fallow every eight years, but vegetable- or jute-based systems’ risk was negligible. However, expanding vegetable-based systems is constrained by higher input costs, lack of capital, labour-intensive practices, market access, and persistent environmental risks. Therefore, multiple strategies are required by public and commercial actors at multiple levels to support smallholders to promote sustainable trade-offs between diverse risks, short-term profitability, and sustainable managing labour, capital, and inputs. The findings highlight the need for agricultural policies and intervention programs to address production technologies, market access, financial services, and extension and training for production and agribusiness skills.