Safari has security settings that can prevent you from consistently streaming music.
The steps and video below will show you how to configure your settings to allow auto-play from Cloud Cover Music.
Change Your Settings to Allow Auto-Play
Log in at tune.cloudcovermusic.com
Click Safari in the top menu bar
Select Settings for This Website
In the menu that appears, click on Stop Media with Sound
Select Allow All Auto-Play
Refresh your window
Click Play Music Here and OK
Note: This change will only affect tune.cloudcovermusic.com. It will not change the auto-play settings for any other website.