[AmberV]

It will work once, but if you do not have both entered, the repeating action will consistently come up as a next action. If you have a sequence of actions that all happen after each other, that means the ones below it will never show up in context view. So you need a start date set to earlier in the day, and a due date set to later (though it seems to work fine if they are the same). That way, it will stay inactive until the start date arrives.