I had been trying to get iTunes to sync photos from my Photos library to the iPhone X for over three months without success. I would always get the same error - “iTunes could not sync because the sync session failed to finish”. After spending countless hours and mostly switching to Google Photos as a way to access all my photos on my iPhone, I finally figured out a fix.
The solution was relatively simple - I had to sync my iPhone X with my work Mac that didn’t have any photos in Photos (what a ridiculous name, btw).
And how did I get here? Read on.
I set up the new iPhone X by restoring it from an iTunes backup of iPhone 7 back in November of 2017. Among other things, it restored over 20,000 photos from the backup. However, after that the iPhone X would never sync reliably with Photos via iTunes and after a couple of successes, it just gave up. It would always fail with the same error. I tried everything the internet told me - restore your phone, restart everything and try, change the lightening cable, change USB ports, take all usb devices out, but to no avail.
I knew the problem was with the photos because that’s the only thing I sync with iTunes. I figured deleting photos on the phone previously synced from iTunes was the key to solving this problem. I tried deleting all the photos on the phone by unchecking sync photos in iTunes. That would not work because of the broken sync. The albums disappeared from iOS Photos App but the photos remained. There is no way, of course, in iOS Photos app to remove photos that were synced previously from iTunes. So I could not get rid of them that way. iTunes won’t get rid of them - because it couldn’t sync and I couldn’t get rid of of them from the phone myself. I even tried to make a new blank photos library and tried iTunes to sync that - but no luck. It would ask if I wanted to delete all photos from the phone - and I’d say yes go ahead - but eventually - “sync failed to finish” is all I’d get.
Four key first-party products - the iPhone X, iOS Photos, iTunes and Photos for Mac - won’t work well together.
Finally - it occurred to me that one way to get rid of all synced content on the phone was to sync your phone to another Mac. So that’s what I did - I tried syncing the phone with my work computer that has no personal data - no photos - and it warned me that I’d lose all my photos previously synced from iTunes and I said - hell yeah - go ahead - and it did. So now I only had photos from the camera roll and that was good.
I got home in the evening - synced photos from iTunes with the phone and it worked just fine! Finally - after three months of struggle - I managed to get my photos from Photos via iTunes to my iPhone X in the iOS Photos app. Phew!
Why don’t I use iCloud Photo Library to sync over the wire instead of using iTunes, a code path that is clearly considered legacy by Apple and is bound to cut off any day? Among other things - its because iCloud Photo Library mandates that all photos (and videos) I take on my phone must end up in my master library. That doesn’t work for me. My phone photos go through Lightroom first, just like my DSLR photos do - and I process them event by event - and after culling, editing and tagging, they make their way to Photos. That’s my workflow. I don’t want my finished product master photo library being cluttered with all and every screenshot, every invoice image and everything else that I take with my phone.
So here we go - iTunes and iMovie really don't sync well with iPhones any more and the only viable code path for the future is the iCloud Photo Library. But there are so many things to dislike about the iCloud Photo Library - least of which is - there is no actual automatic way for me to share it with my family. I have manually create albums and share them. So instead - when I export my finished photos from Lightroom - I start by dumping them in a folder that is being watched by the Google Photos backup program that shoves them into a google photos library. This library is shared by everyone in the family - and everyone gets access to all curated photos as soon as I finish and export them from Lightroom. That's what I do now - until the time Apple makes family sharing a priority and allows me to simply share my library with my family.