Skip to content

Two Days of Tech Support

I ran across a problem where my iPhone wasn’t communicating properly with the Photos app on my Mac. You see, I back up everything locally as opposed to using a cloud service (and then make another backup of that backup through an external drive).

With the release of macOS Catalina (10.15), 32-bit apps are no longer supported. So, older versions of Photoshop (which I heavily relied on), as well as other things, are now incompatible which forces people to find alternatives or upgrade to usually pricier solutions. I’m personally not in the mood to pay between $20-$50/month for Adobe’s Creative Cloud services and apps, so I came across a free, browser-based photo editor called Photopea, which is basically like Photoshop but with a few small differences. However, that’s beside the point.

After removing residual files from my ~/Library folder on my Mac, System Report still yelled at me that I had legacy software installed. However, when I’d go to the paths they were in, nothing would be found. I’d already removed them. Restarts didn’t solve the issue, so after migrating files and folders to an external drive and performing a Time Machine backup on my dedicated Time Machine drive, I took the plunge and rebooted into recovery mode. It was from there that I erased my disk and did a fresh install of Catalina, effectively factory resetting my computer. It now runs good as new, which is fantastic as I’d had almost ten years’ worth of nonsense on there.

After transferring all documents and photos stored on my external back to the computer, and going through an infinite authenticating loop with iCloud, I was finally set up. All mail accounts synced, essential apps re-downloaded from the App Store (and Microsoft Office from my Office account), etc. I was in the clear.

However, when I connected my phone to back up pictures through the Photos app, there were 260 that wouldn’t budge. Photos would see them tagged as “new items” ready for import, I would hit the Import All button, and the app would go through the process of importing them… only for them to remain in the New Items tab, never to be backed up from my phone to the app.

I called Apple Support on Monday, October 28th (I’d discovered this problem on Saturday, the 26th). I was on hold for about a half hour, in the process of being transferred from Joanne, my initial tech support person, to Brian over in the Creative Media department. He did a screen share with me and had me import the photos through the Image Capture app into a folder, and then import the folder into Photos.

Same results. Those 260 refused to budge.

Now, mind you, I consider myself pretty tech-savvy. I had Googled this problem to hell and back. I’d restarted my computer and my phone, repaired my Photos library no fewer than three times, and made sure iCloud Photos was disabled. After calling back and being on hold for another half hour, then becoming irritated as the call dropped, I gave up and resigned to eating dinner. In the interim, I also did yet another fresh install of Catalina. I still got the same results.

Yesterday at the time of me writing this post (which was Tuesday, October 29th, for those of you keeping track at home), I called Apple Support again under the same case number. They’d closed it and had sent me a satisfaction survey from the interactions the previous day, which I had rated probably less than ideal — although the advisor tried his best, he couldn’t come up with a solution.

It was then that Stephanie, my initial advisor, connected me with Chad back in the Creative Media department. I waited a much shorter amount of time than on Monday, and after creating a test administrator account on my computer, syncing the phone to that, and coming up with the same results, he escalated the issue to a Senior Advisor. And so, I met Vincent, one of the Senior Advisors for the Photos app.

Vincent was my saving grace. He’d initiated another screen sharing session, having me open Image Capture yet again. We went through the process of importing the pictures that wouldn’t import to the Photos app into a folder, just as Brian had instructed me to do the day before. Only this time, after locating the pictures in Finder, he had me sort by file kind. We discovered that there were .AAE files, which according to Google, “contains edits made to an image using the Photos app on an iOS device” and “is used to transfer non-destructive edits a user has made to .JPG images in iOS to the macOS system” (source).

Now, Brian had mentioned those files before and gave a (very) brief summary as to what they were, but Vincent went more in-depth. He also had me select every .AAE file and move it to the Trash. I then went back to the Photos app and imported the folder into the library, watching in wonder as batches of images from 2011 through 2014 made their way into the app.

After closing Photos upon completion of the imports, and navigating to my iPhone in the devices tab after reopening it, my New Items section was empty. Removing the .AAE files and importing the .JPGs from a folder had forced Photos to recognize that there was nothing new when I next plugged my phone in — that is, until I took another picture.

As this was a problem that no one I’d spoken to had encountered before, and there were no known reports of it, we resorted to standard troubleshooting methods in order to resolve it. I of course thanked Vincent for his help, and finished importing the rest of the pictures as we had only done two batches together.

Although it took two days and quite a bit of time waiting on hold, I’m so glad we got it figured out. Hopefully, if anyone else ever encounters this issue, this post will help them work through a solution.