This study explored the relationship between user satisfaction and cognitive style as applied to users and systems analysts over the time of system usage. Based on a sample of 62 ‘usersystems’ this study found that the absolute differential in analyst-user cognitive style, or cognitive gap, generally impacts user satisfaction negatively throughout the period of system usage. However, this effect was found to be only particularly strong at two stages of system use; in the third and twenty-first months of system usage. It is thus suggested that analysts should be allocated to users with similar cognitive styles, as one means of optimizing user satisfaction during system usage. Also, that if this precaution is not taken, the system is most likely to stall during the third and twenty-first months of usage. This study thus has important implications for IS team choice during system usage, as well as for system development and maintenance. The results are discussed and conclusions are drawn.