Maps were historically used as tools of the elite to maintain and expand power and control. The development of participatory mapmaking and the geoweb have opened new avenues for broader citizen engagement and therefore challenge traditional power dynamics. This chapter analyzes three examples and presents experiential learning around participatory processes and VGI contributions. Specifically we explore who is contributing their information, what are their motivations and incentives, in what ways do users interact with available technologies, and how is this contributing to change? We conclude by discussing the roles of motivations, the type of contribution, organizational capacity and leadership, and objectives. In comparing and contrasting these case studies we examine the individual and organizational dynamics of engagement, and how this can better inform the discourse about VGI.