Hi, Scott.
By default, you should be able to configure Confluence Server to send notification to a HipChat room when a question is asked within a specific space as mentioned in the Send space notifications to Hipchat documentation.
Can you please confirm if you are using Confluence Cloud instead? If yes, this feature is not available yet as we can see in the screen shot below:
If you have it configured already, can you please confirm if it is sending the notification as expected?
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