As enterprises extend internal systems and applications to external users, it is important to ensure that the user experience operates seamlessly between disparate organizations. To meet this challenge, Federated Identity Management (FIM, also single sign-on) provides an economically efficient and convenient way of providing connectivity to customers, partners, suppliers, and others. FIM is a topic of widespread discussion with rapid growth predicted for almost ten years. This growth has not happened. This prescriptive study identifies some key factors contributing to the slow adoption of FIM technology, including technological complexities, lack of trust between partners, and the complications and expenditures involved in establishing and maintaining contractual agreements between partners.