This paper examines the critical role political processes play in small organizations' software maintenance. To identify political processes, a case study involving two projects (a successful and a failed project) was conducted in a small organization. Analysis of data from the case studies was used to develop insights about the phenomenon which highlight the important role of individuals' political processes in enabling and impeding organizational objectives. Specifically individual's political strategies and styles are explored and their effects on the outcome of software maintenance projects are presented. Preliminary findings of this research suggests that project success is contingent on the emergence of a strong political leadership and that such leadership emerges through synergies in political styles and political strategies of individual actors. © (2012) by the AIS/ICIS Administrative Office All rights reserved.