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Ask iLounge 10-30-09

I purchased an iPod touch 32 GB as an upgrade from my iPod 3G. Since iTunes supports my whole family, I had to clear the authorizations to use my new iPod touch, which was no problem. However, shortly after, I received an iPod touch 64GB as a gift and sold the 32GB. I connected my new 64GB and sychronized it with my library. Now, many of the songs and audio books won’t play on the new iPod. I suspect it is because I’ve exceeded my authorization limit. I understand that I can only clear my authorizations once a year. How do I get my purchased songs and audio books to play on my new iPod? Thanks in advance.

- Ed

To be clear, you do not actually need to specifically authorize your iPod with the iTunes Store as it inherits its authorization automatically from your computer. The five authorization limit only applies to actual computers running iTunes, and not to iPod or iPhone devices. Apple permits you to have an unlimited number of iPod or iPhone devices authorized, provided they’re synced with one of your five authorized computers. When you transfer music from your iTunes library to your iPod, the authorization to play that music goes along with it, provided your computer has already been authorized.

If your computer is not authorized to play your purchased content, then iTunes will simply refuse to transfer those tracks onto the iPod in the first place, so you should not normally find yourself in a situation where the tracks are present but refuse to actually play.

You can troubleshoot this problem further by checking to make sure that your music actually plays on your computer in your iTunes library itself. If your computer is not authorized, iTunes should prompt you to enter your iTunes Store user name and password, after which it should authorize your computer for that particular iTunes Store account. Note that if you have purchased content in your library from more than one iTunes Store account, you will need to authorize each account separately.

Once you have confirmed that iTunes itself can play your purchased tracks, try synchronizing these tracks to your iPod again and see if they will then play properly on your device. Note that you may need to remove these tracks and resync them to your device to ensure that the authorization transfers properly.

If this fails, you can simply try restoring your iPod touch back to factory settings by connecting it to your computer and selecting the “Restore” option in iTunes. This will erase everything on your device and retransfer all of your content from your iTunes library, thus helping to ensure that any authorization information travels along with it.

It’s also worth noting that although you can have an unlimited number of iPods on a single iTunes Store account, you can only have content from a maximum of five different iTunes Store accounts stored on a given iPod. This is presumably to discourage people from visiting many of their friends and transferring purchased items manually from several different iTunes libraries.

My library in iTunes shows around 500 GB but the iTunes Music folder is over 700 GB. Why are they not the same?

- Anonymous

To begin, it’s important to ensure that you are reading your iTunes library size properly. The capacity shown at the bottom of the iTunes window reflects the space taken up by the currently selected items, and will be affected by any filters that you have applied. Further, recent versions of iTunes do not provide any easy method to display all of your content in one listing—different types of media are listed in the different categories such as Music, Movies, etc. Therefore, if you’re viewing your “Music” section, the total capacity shown at the bottom of the iTunes window is only for your actual Music files and does not include other types of content such as Podcasts, Movies, TV Shows, Audiobooks and so forth.

To get a listing of all of the items in your iTunes library for the purposes of a capacity indicator, you can make a Smart Playlist that includes everything, and then read the capacity from the Smart Playlist view. A Smart Playlist with criteria such as Name is not (blank) should suffice for this purpose.

Even if you are looking at the correct capacity information in iTunes, however, it is definitely possible to have more content stored in your iTunes Music folder than is actually listed in your iTunes library.

Firstly, if you add content directly to the iTunes Music folder, the files are of course placed in the folder but iTunes itself does not import these files unless you specifically tell it to, and therefore these new files would not be reflected in your actual iTunes library capacity.

The second scenario is deleting tracks from your iTunes library but leaving them in the iTunes Music folder. This can happen if you choose the “Keep Files” option when deleting tracks from within iTunes itself.

In this case the track gets removed from your iTunes library database, but the file itself will remain in its original location within the iTunes Music folder.

Unfortunately, there is no easy way to determine which files in your iTunes Music folder are orphaned files that are not listed in your iTunes library. However, you can try using the “Consolidate” option described in our article Transferring your iTunes Library to copy your iTunes Music folder to another location. Since the Consolidate option only copies files that are actually listed in your iTunes library, any stray files will be left behind by this process.

Is Apple going to have a software upgrade for those of us that purchased the first 160 GB iPod classic to allow us to use the Genius feature. I think the reason any of us owns this iPod is because we we have a lot of content. It would be nice to make up playlists and mixes without having to go to the computer.

- Guy

Unfortunately, it is extremely unlikely that Apple will ever bring the Genius feature to the original 160 GB iPod classic. With the traditional click wheel iPod models Apple tends to focus its firmware updates on the current models, and has almost never released a software update for a previous discontinued model. Those few updates that have been released for older models in recent years have been limited to fixing serious bugs rather than adding new features. This has been Apple’s approach to the click wheel iPod models going back as far as the fourth-generation iPod, and it has been very common to see new features added even to incremental models like the “5.5G” iPod that are not added to the even the generation immediately prior.

The iPhone and iPod touch have been the notable exceptions here, but this is largely due to the different platform used by these devices and the fact that they use a variation of the actual OS X operating system rather than an embedded firmware that is closely tied to the iPod hardware itself. In other words, previous iPod touch models get new features simply because they happen to already be compatible with the new OS versions that are released for current models.

The bottom line is that when dealing with the click wheel models, you pretty much have to expect that the features you get when you buy the device are the only features that you’re ever going to get.

Hi, I am in a quandary. I have two computers in different states with iTunes on both which necessitated manually managing my music. My iPod will not transfer the music back; when I drag the tune over it won’t do anything. Will my tunes on the iPod be lost if I switch back to Auto Sync? What am I doing wrong? I am so technology challenged.

- Joyce

Unfortunately, iTunes does not allow you to copy music from your iPod back to your computer. The only exception to this is items purchased from the iTunes Store, but even this is an “all-or-nothing” transfer - you can’t select specific items.

To transfer content from your iPod back to your computer, you will need to look at third-party software. Our iPod 201 article, Copying Content from your iPod to your Computer describes how to do this and lists several software packages for this purpose.

Another possible option is to sync the two iTunes libraries themselves so that they contain the same content, and then choose to automatically sync the iPod to the new consolidated library. There are several third-party software applications that can be used to sync iTunes libraries, but if you’re using iTunes 9, the new “Home Sharing” feature can assist you with this directly, without the need for any third-party software. Home Sharing allows you to sync up your iTunes libraries between multiple computers on the same home network.

Note that switching your iPod to automatic sync in this situation would definitely be a bad idea, since this would replace all of the content that is currently on your iPod with the content in the current iTunes library, erasing anything that was on the iPod but not in iTunes. Before doing this you should definitely ensure that you get a single consistent library in place containing all of the tracks that you want to keep on your iPod.

I have an iPhone which I sync with iTunes 9. I am getting an iPod classic to store all my music on. Can I sync both devices with iTunes on the same PC?

- Kerris

Absolutely. There is no real limit to how many iPod or iPhone (or even Apple TV) devices can be connected to the same iTunes library, and you can even connect and sync them all at the same time if you have enough USB ports available.

To set it up, just plug it in. Each device that you connect to your iTunes library gets its own configuration and synchronization settings in iTunes, so you can easily sync different types of content and different playlists to each device, or even sync some devices automatically and manage others manually.

For the purposes of illustration, the image above shows three iPhones, an iPod touch, an iPod classic, three iPod nanos, three iPod shuffles and two Apple TV devices, all connected and synchronizing with the same iTunes library simultaneously.