The paper presents an Actor Network Theory (ANT) account of the development of a Web-based information system (IS) in an insurance company. As an industry-first e-commerce system that transacted insurance products direct to the brokers over the Web, the IS was highly praised by the broker community. Its outstanding success in the marketplace however has been tarnished by internal resentment and objections regarding development costs (over budget), delayed project completion (over time) and poor internal functionality. As a result the IS was seen concurrently as a great success by brokers and some company members (mostly those dealing with brokers) and a resounding failure by company managers. As the IS is of strategic importance for the company, its current unresolved situation and the lack of managers’ commitment to fund its future development, put company at risk and seriously threaten its future competitiveness. By drawing from the ANT account of the IS development we aim to answer How and Why did it come out that the IS became simultaneously a success and a failure? What are the roles of actors, both human and technical, in the production of the IS success and failure?