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Mac: iTunes can’t copy photos from iPhoto

As long-time readers of this blog know, I have a troubled relationship with my Mac, the way some people have a troubled teenager. I love it deeply and tenderly, but sometimes it misbehaves and I just don’t know what to do with it.

The most recent frustration had to do with my iPod. You see, some time ago, I restored my iPod because I kept having this problem where it would flash the “Do not disconnect” screen, but wouldn’t actually sync. I kept having to do a soft reset to get it to start back up again. It usually synced fine the first time, but the second time would require the reset.

I’d like to state right here and now that this blog post does not talk about how to fix that problem. And, in fact, restoring the iPod did not fix the problem. The problem is a minor annoyance and doubtless wears out my iPod faster than normal use. The geniuses at the Apple Genius Bar wanted to fix that problem when I brought in my laptop and described a completely different issue, which is why I even bothered trying to fix it in the first place.

Moving right along, then. After I restored the iPod, I had problems synching it. Most things worked all right, including all my purchased music. But my photos wouldn’t sync. The error I got was that I did not have sufficient permissions to sync. What? I’m the administrator– if i don’t have permission, prompt me for my password, for crying out loud!

Anyway, I dug around. This time, the discussion group over at Apple’s Support website was no help. I saw a lot of iTunes problems and syncing problems, and I saw a couple of people who had the same problem, but no solution for it. Some of the indicators showed that it was related to my iPhoto Library being stored on an external hard drive.

In an unrelated forum post over on the macosx.com forums (having to do with a similar error in iPhoto), I found some advice that people reported as working for a permissions problem in iPhoto. I decided to give it a try in fixing the similar iTunes/iPod permissions problem.

  1. Go to the iPhoto Library on the external hard drive and select File->Get Info. Wait a minute and see how much hard drive space that folder requires.
  2. Clear off enough room on the local hard drive so that you can move the entire folder from the external drive to your internal startup drive.
  3. Drag and drop the entire iPhoto Library from the external hard drive onto your local drive. I put mine inside the /home/username/Pictures folder, where it is when you first get your Mac.
  4. At some point in the copying process, you will be prompted for your administrator password. Enter it and press OK.
  5. Press and hold the Option key while you click the icon to launch iPhoto. You’ll be prompted to find an iPhoto library. Click Choose Library and navigate to the iPhoto Library folder in your local hard drive.
  6. Click OK to open it.
  7. Open iTunes and sync your iPod.

You can now move the entire iPhoto Library folder back to the external hard drive and re-open it (holding down the Option key). The permissions will be fixed and you can continue to sync your iPod even though the library is stored on the external hard drive.

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