This chapter explores the key challenges faced by IT service providers offering after-sales support services to enterprise customers via the Web. The chapter is based on insights provided by representatives of six multi-national IT service organizations. It considers how IT service providers use knowledge-based approaches to offer such services. The chapter highlights the trend towards the employment of networks of business partners to assist with the processes of support delivery. By exploring the perceived needs of the different stakeholders involved in IT support provision, and the transfer of knowledge across these organizations and individuals, the key challenges in IT support provision are identified. The chapter proposes a range of solutions to address the key challenges.