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The next generation of enterprise networks is undergoing major changes as a plethora of new architectures, applications, and services begin to roll out within businesses. In general, the world of voice/telephony, video, and data are "converging" into a global communications network. The purpose of this paper is twofold. First, the design, analysis, and performance of a session initiation protocol (SIP)-based videoconferencing desktop client, which has been developed and deployed over Internet2, is presented. Second, a guideline for managing SIP-based services to be deployed within enterprises, which addresses several challenges in each layer, such as network address translator (NAT)/FW issues, directory service integration issues, and interoperability issues, is proposed. Several detailed experimental results related to interoperability and conformance that were carried out are presented. Findings of extensive SIP/NAT traversal analysis through network traffic measurements are reported. The lessons learned from both the design of a new SIP-based voice/video client, as well as management challenges with enterprise deployment are highlighted.