Individuals learn to use information technologies (IT) in many ways, and some ways are more effective than others. As organizations become more dependent upon IT, the need increases to understand how individuals learn to use IT effectively. In this paper we analyze eight theoretically sampled cases to discover patterns in learning to use IT. Extreme cases were selected in terms of age and IT-competency. Findings suggest that differences in dichotomous learning styles are associated with dichotomous differences in competency and usage behavior (appropriation), while age-based differences were less manifest. Implications for managers, designers, and researchers are discussed.