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This paper proposes a system of using machine learning algorithms to extract communication session information, such as conference bridge number and participant code, from users' emails or appointments. Our system can then use the retrieved information to easily setup a communication session, for example, dialing conference bridge number and participant code, as well as popping up web conference links with simply one click. Our system can also verify the retrieved information by monitoring users' communication sessions. This paper presents the overall architecture and uses the one-click-conferencing feature as an example to illustrate our system.