This paper presents a theoretical framework that can be used to discuss the question of how context, time and different participatory process designs influence the results of participatory monitoring projects in terms of concrete outputs (such as sustainability indicators) and the more intangible social outcomes (such as learning and stakeholder relations). We will discuss and compare four different cases of participatory monitoring of provincial sustainable development in the Netherlands. The results show sustainability issues selected by the stakeholders reflect the socio-economic and ecological structural characteristics of their region. In a different context, stakeholders not only assign different weights to the same set of issues, but more importantly they select a completely different set of regional aims altogether. Since these regional structural characteristics only change slowly over time, the influence of time on stakeholder preferences is shown to be only of minor importance. However, the dissipation of learning effects is shown to be a fundamental challenge for the cyclical nature of participatory monitoring, especially when its goal is shared agenda building. Another important conclusion is that, in the design of participatory processes, more attention should be devoted to providing stakeholders with the opportunity to comment on an 'intermediate' product.