When you make custom schedules and save them, they're saved to the commissioner's HDD. Therefore, when he advances from his phone, where he can't access his xbox/PS3's HDD, then the changes obviously won't show up.
Likewise, if he saves the changes and then tries logging in from someone else's xbox, or has someone else recover his gamertag and then advance for him the changes won't save because, again, they don't have access from his HDD.