iPhone backup in 10.15

With regard to resetting all settings, I know a lot of people are hesitant to try it, but sometimes it does help. No guarantees, of course, but it might work. In light of the fact that this has been going on through different versions of Mac OS, that would seem to indicate that it is something on the phone and not on the Mac. I was just trying to throw out some ideas.

This is similar to a problem that I have run into getting the WiFi sync to work every time when using iTunes. No explanation or reason why it wouldn’t just work.

Did you ever try just backing up without syncing, eject your phone, restart your Mac and then connect the phone again and see if the setting to backup to the Mac was still in place? I am still running an older version of Mac OS X so I still use iTunes. I’m not sure how all this works using the Finder in Catalina.

Something else that you could try is to reset all settings on your phone. Settings>General>Reset>Reset all Settings. You won’t lose any data, but you will have to re-enter all of the device settings again which is a little bit of a PITA, but it’s not as intensive as wiping and then restoring. You will lose all of your WiFi network passwords so they will all have to be entered again. I have reset a settings a few times over the years and it does take a little time and a little work to get all of the settings back to where you had them.

ric_lewis wrote:

A bit of history: this iPhone 11 had its data imported from an iPhone 6+ which in turn had its data imported from an iPhone 4.

I don't remember the last time I ever used 'Reset All Settings'.

Demo, do you think that somewhere in the last 9 years that particular backup setting got a little bit wonky on the phone, which prevented automatic backups in iTunes and then in Catalina?

Yes, I think that if the setting got corrupted years ago, it’s possible that the bad setting just got carried on through each backup over the years. When you restore a backup, you restore your previous settings from that backup, so if a setting is corrupt, you will restore the corrupt setting to the new device.

I’m glad that you finally got things working correctly..

Long shot here but are you sure that your phone isn’t set up to automatically back up to iCloud? If it is, you will have to keep selecting the backup to the Mac option when you backup.