Like many intensive monocultures, some features of banana-based cropping systems may be detrimental to the environment. Pesticide use is a major cause of surface water and groundwater pollution. The risk of water pollution due to pesticides is very high in the insular areas of the French West Indies (FWI). In order to assess these risks and help design more sustainable cropping systems, we propose using an indicator to assess the risk of pesticide pollution over time (Rpest). Rpest provides dynamic assessments through a linkage with a cropping system model that simulates environmental factors and agricultural practices. An expert validation check was conducted and demonstrated that Rpest can rank cropping systems by risk as well as experts. A sensitivity analysis highlighted that the indicator can take the properties of active ingredients and pedoclimatic data into account in assessments. Rpest helps to pinpoint high pollution risk periods. It can also be used to test alternatives and compare systems. This tool can be integrated into a model-based, global, prototyping methodology used for more sustainable cropping systems