This article compares contract farming with share tenancy, another labour regime in which smallholder farmers are bound by contract to deliver produce to another, usually more powerful party. Based on research in the Javanese village of Kaliloro, we explore contracting and sharecropping as labour regimes, each with their own specific mechanisms of surplus transfer from producers to non-producers. The cases compared are sharecropping of irrigated rice, contract farming of watermelon, and contract farming of poultry. There are important differences in how labour inputs are organized, how decisions are made, how costs are divided between landowner/contractor and farmer, and in the mechanisms of surplus transfer between the contracting parties. Exploring these differences allows us to understand and compare the role of the two labour regimes in the penetration of capital into the rural economy. Neither contract farming nor share tenancy are in themselves “win-win” or “win-lose” relationships, good or bad for small-scale cultivators. The actual balance of burdens and benefits—often contravening the provisions of written contracts or state regulation—is determined by power relations between the contracting parties.