Make sure you’ve got extensions
Recently, I took some pictures with a borrowed camera and got some images from the photographer at my wedding. I wasn’t able to upload these images directly off the cameras into iPhoto 6, so I had to import the images later off of a portable drive.
Everything worked fine in iPhoto, and I synced everything up to my video iPod. My intentions were to show off my marriage pictures to family over Easter. When it came time to present the slide show, my marriage photos weren’t on my iPod. Mom was disappointed.
When I got back home, everything was fine in iPhoto and I tried re-syncing to my iPod, but the new photos wouldn’t show up. I thought that maybe the new photos were shot in a raw data format, but I checked my photo library in the Finder and they were all jpgs. Then I noticed that the files didn’t have an extension.
I removed the new pictures from my library and re-imported one with a manually typed ‘.jpg’ at the end and it happily synced-up with my iPod. Yes! Problem solved. Then I realized I had over 100 files to manually add a ‘.jpg’ to and confirm to OSX that I indeed wanted to add an extension to the file. That was going to take forever.
Then I remembered about Automator. I set up a quick name change workflow that added the extension to my files in just a few seconds. I then took my newly renamed files and imported them into iPhoto and now they all live on my iPod. Moral of the story: If you want pictures on your iPod, make sure you’ve got extensions.

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