The sending of email requires that the "Host Settings > Advanced Settings > SMTP Server Settings" be configured and tested properly.  Please check that area first.

Second, in order to use the operator mode, make sure you mark the checkbox "Use Operator Mode?", and also mark the checkbox(es) next to the DNN roles for which you want emails to be sent.

One caveat: emails are ONLY sent to operators IF there is NOT already an operator in the room.  If there is ALREADY an operator in the room, NO emails are sent (DNN SuperUsers such as 'host' are always considered operators regardless of which DNN roles are selected).

Check these three things, and if you continue to have any problems whatsoever, please open a ticket with our helpdesk by sending an email to:  support@swirlhost.com

Thanks!

-- Will Gillen
-- Swirlhost Inc.