Fixing problematic iTunes Match uploads

For months now, I’ve noticed that a few albums I have within my iTunes library that aren’t available to purchase on the iTunes Store were not uploading to iCloud, making them unavailable in iTunes Match. As usual, iTunes provides an almost pointless error message:

This item was not added to iCloud because an error occurred.

On the surface, everything seemed to be working correctly. I knew iTunes Match was enabled and working correctly as many other albums I own that are located within my library uploaded successfully.

I then remembered a somewhat similar issue my girlfriend had with her new iPhone 5s only last week. While syncing music to it for the first time, it reported an error with two songs that iTunes stated could not be synced because the file format was invalid. Strangely, the two songs were part of an album that were encoded in the same format as the rest of the album, (VBR 256k Mpeg-3).

I assumed there was some sort of corruption to the files or that the encoding contained enough errors to trigger an iTunes warning. As the songs played without issue within iTunes anyway, I simply right-clicked the two songs and selected “Create AAC Version” from the contextual menu, then deleted the two original tracks once iTunes had converted them into a new AAC 256k format. After that, the songs then synced to her iPhone.

Going back to my iTunes Match issue, I tried the same method again, thinking that a similar issue was occurring (even though the albums in question were in AAC 256k already). After performing the same action of creating a new AAC version and deleting the original1, the albums were then able to upload to iCloud successfully.

The albums I had this problem with were ripped into my iTunes library a long, long time ago, though it would still have been through iTunes, albeit a very old version. If you’re finding that albums are not uploading to iTunes Match, it’s worth trying the above steps to see if it then lets you upload them.

  1. When creating a new AAC version of the album, don’t deselect any tracks. iTunes will keep the original album highlighted, even after conversion, so that you can easily delete them without needing to check if the tracks are the new AAC version or the original.