If I read that right, then your mistake was stopping it. When you initially plug the car in, it will nearly always start charging immediately. 5-30 seconds after that you should get a notification from your app with your charging window and then up to another 30 seconds after that, it will stop your car charging itself, if its outside of one of those windows of course.
If you stop it however, then it won't be able to start it again itself later on.
Hope that made sense.
I’ve been stoppign it all the time before and its been ok. I figured the app wouldn’t kick in and didn’t want it using too much peak rate.
edit: it set a schedule for 11pm and the tesla app shows its charging so hopefully ok tonight