When setting up an Add a Start Time / End Time Play Rule in a Playlist or Collection, Skykit does not currently support selecting a time period that spans multiple days (ex: 10:00 p.m. - 6:00 a.m.)

If you attempt to save such a time period, you will see an error message reading “Failed to update Entry.”
As a workaround, you can achieve the same goal with multiple Playlist or Collection entries. To do this:
Add your first entry
Set the Play Rule for 10:00 p.m. - 11:59 p.m.
Add a second entry with the same content
Set that entry’s Play Rule for 12:00 a.m. - 6:00 a.m.