The prevailing perspective in the organizational politics literature is that political skill facilitates heightened employee performance. Indeed, meta-analytic results have consistently found a positive relationship between political skill and both task and contextual performance. However, the literature has neglected the possibility of a contingent relationship between political skill and employee performance, despite arguments that organizations are political arenas in which employees also need political will. This is problematic because although politics are described as an ever-present facet of organizations, the extent to which work environments are politicized varies (Pfeffer, 1981), and such contexts can either constrain or enhance organizational behavior (Johns, 2006, 2018). Therefore, underpinned by the multiplicative framework of performance (i.e., P = f(M × A × C); Hirschfeld et al., 2004), we argue that the effects of political skill on employee task and contextual performance are contingent upon employee political will and the degree to which the work context is politicized. Results from a sample of working adults and their supervisors provided support for our hypothesis. Namely, political skill and political will interacted to predict heightened levels of task performance and citizenship behavior within more political contexts, but not within less political contexts. The contributions of this study to the politics literature are discussed commensurate with this study's associated strengths and limitations. (PsycInfo Database Record (c) 2024 APA, all rights reserved).