Organizational citizenship behavior (OCB) has attracted major research effort for the last two decades. The vast majority of studies of OCB have been devoted to affiliative forms of such behavior including interpersonal helping, courtesy, and compliance, which are intended to maintain and reinforce the status quo. The present study attends to another form of OCB that challenges the status quo through suggestions for constructive changes in work methods, processes, and policies. This study identifies a set of workplace characteristics that predict change-oriented OCB. Multi-level analyses of large-scale longitudinal data showed that strong vision and innovative climate predicted change-oriented OCB via both individual- and cross-level processes. These contextual influences were mediated by two intervening variables: psychological empowerment and felt responsibility for change. The results suggest that change-oriented OCB is significantly predicted by only organizational characteristics. Group-level dynamics may be less important for understanding challenging types of OCB than for affiliative types such as helping or compliance. Copyright © 2007 John Wiley & Sons, Ltd.