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The willingness of Knowledge Management System (KMS) users to use the systems has been mentioned as one of the major factors determining effectiveness in the system's usage. Therefore, the development of autonomous (personal or volitional) motivation towards KMS use is conceptualized in this study to be dependent on factors inherent in the system and the cultural values that dominate the system's (KMS) environment. By relying on 306 responses from KMS users, linkage quality and knowledge richness of KMS are two characteristics found to be major predictors of autonomous motivation to use the systems, while cultural values for innovativeness also plays prominent role in developing autonomous motivation to system use. In retrospect, the developed autonomous motivation to use was found to be a high predictor of KMS usage.