>You don't want your users to worry they are hurting their help desk chat bot when closing the window

We're already there. A couple of years ago Bradesco, a large Brazilian bank, programmed its bot to talk back to abusers. Instead of "sorry, I don't understand", it says things like "don't talk to me like that"

https://www.trendwatching.com/innovation-of-the-day-brazilia...