The success of organizational change increasingly depends on employees taking personal responsibility for change through effective adaptation to changing conditions and proactive anticipation of new challenges. In this study, we examined how work context features influence the change-oriented behaviors of adaptivity and proactivity in the workplace. We proposed several direct and moderating effects of job context variables on adaptive and proactive behaviors. We used a multilevel design and a unique data set with 621 special education teachers embedded in 157 urban public schools to test our hypotheses. Our analyses show that adaptive and proactive behaviors are distinct aspects of job performance during organizational change and that different job features have distinct direct and moderating effects on these behaviors. Our results provide insights into how leaders of change efforts can create a work context that encourages employees to actively participate in the change process.