Written by: Andrew Lardi
Categories: Hints & Tips
With iTunes 7, Apple has given users the ability to sync the songs in their “Purchased” category between multiple machines. The biggest complaint about this feature is that it only lets you transfer songs that are from the iTunes Store, however much like the “analog hole” Apple has also given us a work around.
If you’re the kind of person that likes having a playlist of all your purchased music, the default purchases playlist will no longer fit your needs. So before we get going, you may want to make a smart playlist with “Kind contains protected†as the rule. This playlist is handy to have even if you don’t use it on a daily basis, so I highly suggest you make one eventually. Now that you’ve done that, just follow these instructions:
Step 1: Select all files in the category you choose (Music, TV Shows, Movies, Podcasts, or Audiobooks are compatible with this method).
Step 2: Drag and drop those files onto the “Purchased” category.
Step 3: To keep it up to date just periodically drag your “Recently Added” playlist to “Purchased” or do so manually. Keeping up with your music is the most tedious part of this method.
Once you do this you will be able to transfer your media to multiple machines. This will work with Automatic or Manual Syncing. If you would like your iPod to transfer files between PC and Mac iTunes, you are going to have to format your iPod with Windows, and then do this method. A Windows formated iPod will sync with a Mac for it’s main machine. The only drawback with this is that Windows formatted iPods are in FAT32, meaning the name of the iPod will show up as all capital letters in OS X even after renaming it.


















I hate you, I did not realize how many tunes I had purchased from iTunes, now I know and it ain’t pretty.
Positive Dennis
This seems odd. You just create a playlist called “Purchased” and anything you put in there will be restored like iTS songs? It just seems too easy a solution.
How does iTunes know which “Purchaed” playlist to read? Are you supposed to delete the default “Purchased” playlist?
I think you may have misread. The article is speaking about the existing “purchased” category that is in iTunes. Making a playlist called “Purchased Music” is only for setting a rule that protected music have it’s own separate playlist. The Purchased category will not contain all songs even those you did not purchase, which are not protected.
Oddly enough the Maccast podcast appears in the protected category. I wonder why? And yes I did what was suggested and the category is “protected” not “purchased.”
Positive Dennis
The MacCast is presented in Audiobook format. Adam names the files in M4B with is an AAC file that is set as an Audiobook. Audiobooks are ONLY protected the way itunes does them. The good side of that is that you can listen to them in low or high speed.
The iTunes Purchased catagory is able to contain non any file because they want you to be able to add music you may have had backed up on a disc and have them show up in your purchased catagory. If you just add a protected file to the library it wont show up under Purchased right away.
I know that I can not save an audiobook as an MP3 file on a disk. (This is one reason I do not get any). So then I can not save MacCast as an MP3 and save it to a cd? This seems odd, not that I would likely do that.
These DRM issues are in general very confusing and prevent me from purchasing iTunes video products.
Positive Dennis