This paper explores the significant challenges and opportunities in extending Internet2 middleware tools such as Shibboleth, Signet and Grouper, in a medical information environment. Shibboleth is an open-standards-based solution that meets the requirements of organizations that need secure federated authentication and authorization services to protect the privacy of their information. Signet is a tool used to store and manage authorization data across an enterprise or virtual organization. Grouper is a tool used to create and manage group information used in a wide variety of information system contexts. These tools emerged out of middleware initiatives funded by the National Science Foundation and Internet2 to solve problems common in inter-institutional application environments. Middleware initiatives seek to enable organizations that need to exchange information including higher education, scholarly information service providers, medical research and health care institutions, digital content providers, federal agencies and others that interact in higher education and medical environments. The presenter is engaged with a team of researchers at Georgetown's Imaging Science and Information Systems (ISIS) Center, Georgetown University Hospital, Washington Hospital Center, and the District of Columbia Department of Health to extend Internet2 middleware tools in Project Sentinel computing environments. Project Sentinel is a multiyear bio-surveillance and bio-terrorism defense research project, funded by the National Library of Medicine. The Project Sentinel Collaboratory contains web services-based, client/server and GRID-based information systems. Extension of internet2 toolsets in each of these environments comes with a varying degree of technical complexity but also with functional and organizational issues that must be resolved. Successful extension of these tools brings the promise of noteworthy inter-organizational data sharing and analysis in the context of well architected strategies and policies that are scaleable and address information security, authentication and authorization issues in meaningful ways. (c) 2005 Published by Elsevier B.V.