Extensive research has been conducted on information systems outsourcing, and the major concerns of these studies can be classified into three categories: first, research on the determinants of outsourcing; second, research on the benefits and risks of outsourcing; and third, research on outsourcing contracts. However, despite the long and widespread application of information systems outsourcing, related research has not adequately reflected changes in outsourcing forms or trends. This study redefined the factors perceived to have moderating effects on the relationship between organizational information systems outsourcing and performance through a review of existing literature, proposed a comprehensive analytical model for conducting the research, and aimed to empirically verify whether this research model of effect relationships is applicable to the reality of Korean firms. The major findings verified through empirical analysis are summarized as follows. First, regarding the moderating effect of organizational size on the relationship between information systems outsourcing and outsourcing performance, organizational size was found to have a significant relationship with outsourcing performance for information systems development functions; however, no moderating effect was found for management functions. Second, vendor influence was found to have no significant relationship with information systems development functions through outsourcing, but was found to have a considerable impact on management functions. Third, the innovativeness of the adopted system was found to have a moderating effect on both information systems development and management functions through outsourcing. Meanwhile, the level of top management support for the information systems department had a moderating effect on information systems development functions through outsourcing, but showed no moderating effect on information systems management functions.