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I have followed the process without success. I know I need to authorize calendar access on the iPhone under settings - privacy. But I do not see an option to authorize access !
When my S's calendar has not synched in a while I can get it to synch by connecting to the car using the Tesla app on my iPhone. Just connecting the app seems to force the calendar to synch. Works pretty much every time.
I've found that the only reliable method is to make sure the calendar is updated before you go to the car the first time that day. (Update the phone's calendar the night before.) Updating it after the first driving session almost never works.
Thanks for the tips. Mine stopped syncing after the last update - .28.. Getting new update as I write this. If it's still out of whack, I will try the advice given above.