Payments for watershed services (PWS) are schemes that use funds from water users (including governments) as an incentive for landholders to improve their land management practices. They are increasingly seen as a viable policy alternative to watershed management issues, and a means of addressing chronic problems such as declining water flows, deteriorating water quality and flooding. In some places, local governments, donor agencies and NGOs are actively trying to upscale and replicate PWS schemes across the area. While their apparent success and progress in launching new initiatives is encouraging, there is still much to be learned from formative experiences in this field, especially with regard to monitoring and evaluation. In this paper we discuss the monitoring and evaluation criteria behind compliance or transactional monitoring, which ensures that contracts are followed, and effectiveness conditionality, which looks at how schemes manage to achieve their environmental objectives regardless of the degree of compliance. Although the two are usually linked, a high degree of compliance does not necessarily ensure that a scheme is effective. This is because a poorly designed scheme may target the wrong land managers and land that is at least risk, meaning that payments do not generate the desired hydro-ecological or conservation benefits. As the levering capacity to demand payments for better watershed management increases, so does the need to understand the dynamics of such activities and demonstrate their impacts. While the growing interest in such schemes shows that participants believe in the principle of land management, evidence of their impact is needed to determine which initiatives genuinely add value and are worth pursuing.