Copy iPod Music to Your Mac Using OS X Lion and iTunes 10

There are many reasons why you might want to copy music from your iPod to your Mac. For example, if you suffer data loss on your Mac, your iPod may hold the only copy of hundreds or thousands of your favorite tunes. If you buy a new Mac, you'll want an easy way to install your music. Or if you delete a tune from your Mac by accident, you can grab a copy from your iPod.

Whatever your reasons for wanting to copy music from your iPod to your Mac, you'll be happy to hear that the process is a simple one.

What You Need

This guide was written and tested using OS X Lion 10.7.3 and iTunes 10.6.1. The guide should work with later versions of both OS X and iTunes.

Here's what you'll need:

• An iPod that contains your music.
• A Mac with OS X Lion or later.
• A Mac with iTunes 10.6.1 or later.
• An iPod USB/syncing cable.

A quick note: If you're using a different version of iTunes or OS X? Then take a look at: Restore Your iTunes Music Library by Copying the Music From Your iPod.

Disable Automatic iPod Syncing With iTunes

Apple tries to make syncing your iPod and the iTunes music on your Mac as simple as possible by automatically keeping your iTunes library and your iPod in sync. This is normally a good thing, but in this case, we want to prevent automatic syncing. Why? Because if your iTunes music library is empty, or missing a specific song, it's possible that if you allow your iPod and your iTunes library to sync, the process will remove the songs that are missing from your Mac from your iPod.

Here's how to avoid that possibility.

Turn iTunes Automatic Syncing Off

1. Make sure your iPod is NOT connected to your Mac.
2. Launch iTunes.
3. From the iTunes menu, select iTunes, Preferences.
4. In the iTunes Preferences window that opens, click on the Devices icon at the top right-hand side of the window.
5. Place a check mark in the "Prevent iPods, iPhones, and iPads from syncing automatically" box.
6. Click the OK button.

Transfer iTunes Purchases From Your iPod

Your iPod probably contains music you have purchased from the iTunes Store as well as tunes you have acquired from other sources, such as CDs you've ripped or songs you purchased from other sources.

If you purchased all of your music from the iTunes Store, use this step to automatically transfer purchases from your iPod to your Mac.

If your music comes from a variety of sources, use the manual transfer method outlined in the next step instead.

Transfer Purchased Music

1. Make sure iTunes isn't running.
2. Make sure your iPod isn't connected to your Mac.
3. Hold down the option and command (Apple/cloverleaf) keys and plug your iPod into your Mac.
4. iTunes will launch and display a dialog box telling you that it's running in Safe Mode. Once you see the dialog box, you can release the option and command keys.
5. Click the Continue button in the dialog box.
6. A new dialog box will appear, giving you the option to either "Transfer Purchases" or "Erase and Sync." Do NOT click the Erase and Sync button; this will cause all of the data on your iPod to be erased.
7. Click the Transfer Purchases button.
8. If iTunes finds any purchased music that your iTunes library is not authorized to play, you will be asked to Authorize it. This happens if you have songs on your iPod that came from a shared iTunes library.
9. Click Authorize and provide the requested information, or click Cancel and the transfer will continue for files that don't require authorization.

Manually Transfer Music, Movies, and Other Files From Your iPod to Your Mac

Manually transferring content may be the best way to get your music, movies, and files from your iPod to your Mac. This is especially true if your iPod contains a mix of items purchased from the iTunes Store and content obtained from other sources, such as ripped from a CD. By manually copying the content from your iPod to your Mac, you ensure that everything gets transferred, and that you don't have duplicates in your iTunes library, which can happen if you use iTunes to automatically transfer purchased content and manually transfer everything else.

If all of the content on your iPod was purchased from the iTunes Store, see pages 1 through 3 of this guide for instructions on using the built-in iTunes transfer system.

Manually Transferring Your iPod Content to Your Mac

1. Quit iTunes if it's open.
2. Follow the iTunes setup instructions on pages 1 and 2 of this guide.
3. Ensure that your iPod is not connected to your Mac.
4. Hold down the option and command (Apple/cloverleaf) keys, and then plug your iPod into your Mac.
5. iTunes will display a dialog box warning you that it's running in Safe Mode.
6. Click the Quit button.
7. iTunes will quit, and your iPod will be mounted on your Mac desktop.
8. If you don't see your iPod on the Desktop, try selecting Go, Go to Folder from the Finder menu and then entering /Volumes. Your iPod should be visible in the /Volumes folder.

Make Your iPod Files Visible

Even though the iPod is mounted on the desktop, if you double-click on the iPod icon to see the files and folders it contains, no information will display; the iPod will appear to be blank.

Don't worry, that's not the case; the information is just hidden. We'll use Terminal to make the files and folders visible.

1. Launch Terminal, located at /Applications/Utilities.
2. Type or copy/paste the following two commands into the Terminal window, next to the Terminal prompt. Press the return or enter key after you enter each line.

defaults write com.apple.finder AppleShowAllFiles TRUE

killall Finder

Once you enter the above two commands, the iPod window, which used to be blank, will display a number of folders.

Where Are the iPod's Music Files?

Now that we've told the Finder to display all of the files and folders on your iPod, you can browse its data as if it were an external drive connected to your Mac.

1. If you haven't already done so, double-click the iPod icon.
2. You will see a number of folders; the one we're interested in is called iPod_Control. Double-click the iPod_Control folder.
3. If the folder doesn't open when you double-click it, you can access the folder by changing the Finder view to List or Column. For some reason, OS X Mountain Lion's Finder won't always allow hidden folders to open in Icon view.

1. Double-click the Music folder.

The Music folder contains your music, movies, and videos. However, the folders that contain your content use a simplistic naming system, usually F00, F01, F02, etc.

If you peek inside the F folders, you will see your music, movies, and videos. Each folder corresponds to a playlist. The files within the folders also have generic names, such as JWUJ.mp4 or JDZK.m4a. This makes figuring out which files are which a bit of an ordeal.

Luckily, you don't need to figure it out. Although the files don't have song or other titles in their names, all of this information is preserved within the files in ID3 tags. All you need to sort them out is an app that can read ID3 tags. As luck would have it, iTunes can read ID3 tags just fine.

Copy the iPod Files

The easiest way to proceed is to use the Finder to copy all of the files from the F folders to your Mac. I suggest you copy them all to a single folder called iPod Recovery.

1. Right-click a blank area on the desktop and select New Folder from the pop-up menu.

1. Name the new folder iPod Recovery.
2. Drag the files located in each of the F folders on your iPod to the iPod Recovery folder on the desktop. The easiest way to do this is to open each F folder on the iPod, one at a time, choose Select All from the Finder's Edit menu, and then drag the selection to the iPod Recovery folder. Repeat for each F folder on the iPod.

If you have a lot of content on your iPod, it may take some time to copy all of the files.

Now that we copied all of your iPod content to a folder on your Mac desktop, we're finished with the iPod. We need to unmount the device and disconnect it from your Mac.

1. Right-click the iPod icon on the desktop and select Eject (your iPod's name). Once the iPod icon disappears from the desktop, you can disconnect it from your Mac.

Get iTunes Ready to Copy Data to Its Library

1. Launch iTunes.
2. Select Preferences from the iTunes menu.

1. Click the Advanced icon in the iTunes Preferences window.
2. Place a check mark in the "Keep iTunes Media folder organized" box.
3. Place a check mark in the "Copy files to iTunes Media folder when adding to library" box.
4. Click the OK button.

Adding Your iPod Recovery Files to iTunes

1. Select "Add to Library" from the iTunes File menu.
2. Browse to the iPod Recovery folder on the desktop.
3. Click the Open button.

iTunes will copy the files to the iTunes library. It will also read the ID3 tags and set each file's title, genre, artist, and album information, according to the tag data.

Once you've completed the copying process in the previous step, your iTunes library is ready to use. All of your iPod files have been copied to iTunes; all that's left is do a bit of cleanup.

You'll notice that while all of your files are in the iTunes library, most of your playlists are missing. iTunes can recreate a few playlists based on ID3 tag data, such as Top Rated and by Genre, but beyond that, you'll have to manually recreate your playlists.

The rest of the cleanup process is simpler; you just need to restore the Finder's default settings to hide certain files and folders.

Hide Files and Folders

1. Launch Terminal, located at /Applications/Utilities.
2. Type or copy/paste the following two commands into the Terminal window, next to the Terminal prompt. Press the return or enter key after you enter each line.

defaults write com.apple.finder AppleShowAllFiles FALSE

killall Finder

Once you execute these two commands, the Finder will be back to normal, and will hide special system files and folders.

iPod Recovery Folder

You no longer need the iPod Recovery folder you created earlier; you can delete it whenever you wish. I recommend waiting a brief time, just to make sure everything is working properly. You can then delete the folder to free up some disk space.

One last point. Manually copying your iPod's content doesn't remove any digital rights management from files that have it. You will need to authorize iTunes to play these files. You can do so by selecting "Authorize This Computer" from the iTunes Store menu.

Now it's time to kick back and enjoy some music.