This paper presents the findings of 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 its successful transition from a socialist company operating in a protected market to a privatized company operating in a capitalist global market, as well as the pivotal role of information technology (IT)-supported organizational learning that brought about radical change and successful transition. Our investigation of Sava's experiences demonstrates how the company's increasing attention to organizational learning, integration of working and learning, and its constant innovation of products and processes created new needs for IT support that motivated the adoption of new IT systems (such as Lotus Notes, document management systems, SAP), which in turn increased Sava's capacity to learn. Furthermore, our study reveals how the role of IT systems in organizational learning depends on the nature of learning (single-loop, double-loop or triple-loop learning) and the organizational level at which learning takes place (individual, group/department or organization). By providing insight into the emergence of distinct types of ITsupported learning and their vital role in Sava's successful transition, the paper contributes to a deeper understanding of the relationship between IT and organizational learning that is relevant and inspiring to other companies, especially those operating in transition economies. ž č čWe dedicate this paper to the memory of Dubravka's late father Momir Cecez who left us too soon to see how his recent book and personal experiences in building the Yugoslav economic system helped us understand Sava's history and the broader context of its transition.