(Unless your wife doesn’t mind going through the privacy and location dialogs for her apps again.) Mind you, it may not be what the issue is, so that’s why I suggest trying this last. If that is somehow corrupted, this may allow the phone to re-establish a trust relationship with an iTunes library. However, the other thing this does is to delete the iTunes pairing relationship that the phone has stored. The main function of this is to reset all of the privacy and location preferences for your apps on the phone, so this will be a bit of a pain - the first time that you run a third party app that needs access to location or a privacy permission, it will ask for that permission. This is a bit of a nuclear option, but after you exhaust everything else, there is an option on the iPhone - settings / general / reset / reset location & privacy. If her phone falls under a truck all her data will be gone. And of course iTunes offers zero indication as to what the user should do to fix the issue. So now she cannot sync iTunes content to her iPhone. I did that too and I’m not encountering any of these issues on my Mac. And the iPhone hasn’t done anything apart from the 12.1.1 update. I cannot recall any software updating activity within the last few months on her old Mac. The last iTunes backup carried that time stamp so until most recently everything worked just fine. She usually hooks it up to iTunes about once a week to do a backup and sync. We tried syncing over USB (even tried different ports) and over wifi. ![]() Rebooted Mac in Safe Mode and tried iTunes there. So after searching the web we tried a few things. Let alone give you any idea as to what you’re supposed to fix. ![]() iTunes will start the sync, but then complain that the sync “could not be synced because the sync session failed to start”. My wife’s iPhone SE (the latest iOS 12.1.1) will no longer sync with her Mac (2009 13" MBP, El Cap with the latest iTunes supported on that OS).
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