From 1985 to 2002, most Federal conservation dollars going to farm operators have been to retire land from crop production. Yet most U.S. farmland (850 million acres) remains in active production. The Farm Security and Rural Investment (FSRI) Act of 2002 sharply increased conservation funding and earmarked most of the increase for working-land payment programs (WLPPs). The design and implementation of WLPPs will largely determine the extent to which environmental goals are achieved and whether they are cost effective. We simulate potential environmental gains as well as adjustments in agricultural production, price, and income associated with various WLPP features to illustrate tradeoffs arising from WLPP design and implementation. Competitive bidding with the use of environmental indices to rank producers for enrollment is most cost effective. Payments based on past conservation will help support farm incomes, but limit the amount of additional environmental benefit that can be generated under a fixed budget.