Migrating an iPhoto Library to an iCloud Photo Library: A Story of Frustration

When Apple is at its best, it works seamlessly. You don’t have to think about It. It just, to beat a cliche a little deeper into the ground, works. But when it doesn’t work, it’s a smelly bag of frustration — especially if it’s a new update that just shipped.

Earlier this morning, I received a notification from the MacRumors.com’s Twitter feed that Yosemite 10.10.3 is ready for download. I was looking forward to this upgrade because iPhotos was going to become Photos and the years of stills and videos I’ve collected over the years would live in the cloud.

This is a big deal to me, because my iPhoto library lives on an external hard drive. Fitting everything on my MacBook Air’s SSD just isn’t doable. Being able to access all my photos and albums — which, to be fair, is made up of a lot of photos of my cats — while not having to worry about the space its taking up on that precious, precious flash storage space has been a dream.

Yosemite 10.10.3 downloaded and installed. I had some other things to take care of, but I eventually opened the Photo app after buying some additional iCloud storage. There was a quick introduction, and I was in. Things started uploading. Hey, my days of having my photos on a separate hard drive were over!

Then it stopped at 224 photos. I couldn’t tell you how many photos I have in my iPhoto library, but I know that a conservative guesstimate would be at least 10 times that number. (It’s actually 5,212; most cat photos.)

Ryan Ozawa, founder of this site, was fresh off his Geek Beat segment on Hawaii News Now. He figured my problem had to do with uploads being done incrementally. I nodded (though he couldn’t see it because we were texting). It made sense. He used the Yosemite 10.10.3 public beta and, by extension, the Photos beta, so he’d know about these things. Besides, who knew how many people were trying to upload their cat photos at the same time? I can haz bandwidth?

But some things didn’t make sense. There was an import option, but I couldn’t select my iPhoto library. I tried calling AppleCare, but when the person I spoke to found out my MacBook Air that was no longer covered, I was asked if I wanted to buy additional coverage so I could talk to someone about my problem. Or I could see a Genius.

I declined. I Googled my problem but apparently, I had a very unique problem. There was some nitpicking about the OS X Photos app, but no one seemed to have my problem. Also, those problems were all related to the public beta.

Breaking down, I called Apple Care again. Instead of being nice to the automated attendant, I pounded on the 0 key and said “Operator”. Ultimately, the cheery, non-corporeal synthesized voice got the message I wanted to speak to someone real.

The first person I spoke to specialized in iOS products. Obviously, he wasn’t of much help, but in that very Apple way, he was polite and tried to do everything he could. I made sure to tell him that I was sure this wasn’t a hardware problem, this was a problem with a new piece of software tied to their cloud services. Luckily, he got it and didn’t ask for a credit card number for additional help.

iOS Support Guy came to the end of what he could do for me after a few minutes. He transferred me to someone in “CPUs”. I explained my problem again, he said he needed to research the problem and could I wait on hold.

Sure. He came back on after a few minutes, and from his tone, I could tell I’m probably the first one calling about this problem. We opened up a remote desktop session, and while on the phone with him I say that I could open the iPhoto Library package and transfer over the images to Photos, but that doesn’t seem like the sort of elegant solution I expected from the company.

He agreed. But Photos is as new to him as it is to me. Apple hasn’t given any of their Apple Care people know about the release of 10.10.3 and Photos. Ultimately, he tells me that I should transfer over the image folders, which are arranged by year. It works, but there’s none of my metadata — who’s who from facial recognition, albums, that sort of thing. It dawns on me that the advice I got was, essentially, moving the photos from the iPhoto Library into Photos. It was the very inelegant solution I wasn’t looking for to begin with.

I tried an trick to open a different library in iPhoto on Photos by holding down the Option key while I started up the application. It worked. My older iPhoto Library, on my external hard drive showed up in the pop-up menu.

Hey, this could work! I selected it and Photos transitioned the iPhoto Library’s database, metadata and this and that into a format it could read. But so far as I could tell, it wasn’t uploading to iCloud…which was  the point.

I poked around in Photo’s preferences. I noticed that the iCloud menu sternly said that the iCloud options weren’t available unless the library was on the system drive.

Well that didn’t make sense. Didn’t all the images live happily on the cloud? You know, happy like the images and videos of my cats that I’d be able to access anywhere.

Then it struck me. Things were complicated. When the iCloud menu did work on Photos’ preferences, it gave an option to keep a full resolution copy of the images on the drive or to keep a minimized version of the images. It would still require local storage. My dream of living in the cloud — at least the iCloud — was dashed.

So to reiterate:

  • The Photo Library must be on the system disk
  • It won’t upload to iCloud if your library is on an external drive
  • iCloud Photo Storage requires local storage space
  • It’s not a pure, in-the-cloud solution, at least for OS X


I’d paid for the additional storage and I’d invested time into figuring this out, so I pressed on. I deleted episodes on iTunes that I hadn’t watched. (My iTunes library was still on my system disk.) I moved my mobile apps folder (~/music/ITunes/iTunes Music/Mobile Apps) to an external hard drive and deleted off the system drive. (I could restore it from Time Machine, but I like to have duplicates, just in case.)

I transferred the Photos Library from the external drive to the system drive. The images are now uploading. If I’m correct, the “Optimize Storage Space” will allow me to drop the Mobile Apps folder back my iTunes Library, though I’ll probably have to keep my episodes deleted until I upgrade. (My library is in the process of uploading so I’ll update as to any space savings, is any, there actually is.)

So if you have an iPhoto Library on an external drive and you want to transition to iCloud Photos Library:

  1. Clear up the space for the library on your system drive, if you can
  2. Buy additional iCloud storage, if needed
  3. Move the iPhoto Library to your system drive — preferably to the Pictures folder in your user account (~/Pictures)
  4. Hold the Option key down and start Photos
  5. Select the library you just moved
  6. Let Photos do its (upload) thing

I’m still not entirely happy with this solution. iCloud Photo Library has the most appeal to people like me — people who are low on storage space to begin with. Making them free up enough space to use the service doesn’t seem like a catch-22, it’s contradictory. Keeping any kind of copy of the images in addition to metadata and database information on a local drive just seems like an even bigger head scratcher.

Photo by Christopher Aloi (ctaloi)/flickr.

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