I have only seen this when a game disconnects or freezes. It basically meas the game never counted or was never played hence on the schedule it will say playable and will not be needed to be reset where as the challenge failed issue caused the game "to be in progress" until it was reset. I hope that answers your question. Although I am not sure why that would continue to happen to one person. Last year we had wacky issues like that and sometimes dropping said user and re-inviting him fix the problem....you may want to try that.