Take a look at the boilerplate plugin for Mibew Messenger
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The first. Mibew works fine only with Apache. We did not test it on IIS and do not plan to.The second. It's obviously that your environment is not configured correctly to work with SEF URL. Thus you can try to use links like http://chat.mysite.com/index.php/operator (notice index.php part). Nevertheless, I cannot guarantee that everything will work fine because, as I've said before, we did not test Mibew with IIS.