Contingency theory suggests that various environmental, organizational and managerial factors will influence an organization’s approach to IT management. This chapter discusses the contingent nature of information systems strategic planning (ISSP) practices and presents the results of an empirical study of ISSP and the role of IS within 90 leading companies in South Africa. Results of a partial least squares analysis demonstrate the significant effect that perceptions of the future strategic role of IS within an organization have on ISSP behavior. Moreover, it was found that those organizations in the strategic quadrant of the McFarlan grid emphasized ISSP activities, committed more resources to the ISSP process and attributed greater importance to ISSP-business strategic planning integration mechanisms, than those organizations in the other quadrants of the grid. The relationship between ISSP and IS function performance was also significantly higher for firms in the strategic IS environment.