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In Live Agent, it is possible for a Supervisor to send a private message to an Agent. What about the other way round? I'm not talking about the flag to request help, but an actual private back and forth chat.

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You have to use the Pre Chat API for that, and add a form to your webpage. You find a Pre Chat Form Code Sample in the Live Agent Developer's Guide, including a "Chat Now" button for the website visitor to click. It will look like this without any formatting / CSS styling done:

Remember to allow access to the Pre Chat API in the Agent configuration of your Live Chat Deployment.

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