Depleting water resources is a widespread problem across the Kansas High Plains aquifer. The value of irrigation is accentuated due to lack of surface water and low precipitation in western Kansas. Accelerated groundwater withdrawals for irrigation caused a further decline in the saturated thickness of the aquifer. To encourage water conservation and reduce further depletion of the aquifer, federal and state cost-share programs have subsidized irrigation technology upgrades. However, this effort may have been undermined by producers who increased their water usage for irrigation with water-intensive crops. A simulation model comprised of an irrigation scheduling tool coupled with a crop yield simulator are used to predict risk-efficient crop and technology choices, which allows us to estimate the effect of an irrigation technology upgrade on the aquifer. This research characterizes producers’ decisions to maintain economic viability while adapting to limited irrigation conditions. The study will identify the conditions under which technology upgrades will both save water and increase farmers’ returns from irrigation. The study also estimates the threshold payments to farmers to switch to relatively less water-intensive crops that will promote water conservation on the High Plains aquifer.