The relationship between information systems (IS) and organisational learning has long been claimed but not sufficiently empirically grounded (Robey et al., 2000). This paper examines this relationship by drawing on a longitudinal study of the Slovenian company Sava during its 1995-2004 transition period when it adapted to and prospered in a free market economy. The company is particularly interesting because of the pivotal role information systems (IS) played in supporting organisational learning during its successful transition from a socialist company operating in a protected market to a privatized company operating in a capitalist global market. By providing insights into the role of various IS in organisational learning and in the company’s successful transition, the paper contributes to a deeper understanding of the relationship between IS and organisational learning which is relevant and inspiring to other companies, especially those undergoing radical change.