The effects of cross-compliance depend on the strategies of participation/compliance of farmers, as well as on the ability of public administration to design appropriate policy mechanisms. The objective of this paper is to present a framework for the analysis of cross-compliance under asymmetric information with the option of differentiating commitments across farmers. The methodology is applied to a case study represented by the province of Bologna (Italy). The results show that, in the present conditions of control and sanctions, only a small share of farms is interested in complying with cross-compliance. The profitability of the choice of compliance/non-compliance depends mainly on the amount of single farm payment entitlements compared with the total land. The differentiation of restrictions across farmers, under relevant budget constraints for controls, appears a key strategic components in order to ensure the effectiveness of cross-compliance.