The Web and other digital technologies are bringing unprecedented changes to the ways in which enterprises carry out their business, and heightening the nature and degree of competition they face. This paper reports upon an interview-based survey which investigated changing business models in the commercial print industry. It explores the fundamental reasons some of these new Web-based models are failing. Key factors include the complex and highly changeable nature of print workflows: these mandate a high degree of human involvement, which failing Web- based models have excluded. It discusses some of the ways in which the adoption of different forms of digital technology is changing the customer-supplier relationship and introducing new uncertainties into it, and concludes with a discussion of the need for software to provide management support, in the broadest sense, for complex, changeable inter- organisational workflows. 8 Pages