How to Autofill your iPod Shuffle from your iPod Or iPod Mini

In last week’s article, I took a look inside the invisible folder on the iPod Shuffle and talked about methods for moving your music off of your iPod / iPod mini / iPod Shuffle and back to your Mac. This week, I’m going to walk you through how to set up iTunes so that you can choose to Autofill your iPod Shuffle directly from your iPod, without having to copy all those files back to your hard drive. This is very useful for someone like myself, who works off of a 12-inch Powerbook with only 2GBs of music on my internal 60GB hard drive, but with nearly 32GB of music on my 4G 40GB iPod. These directions will center on the Mac side of things, but everything I’m doing here should be doable on a Windows XP box, so everyone, please, read along.

The majority of this is setup. Once you go through these steps and have everything set up, you can easily Autofill your iPod Shuffle from your iPod whenever you like, by simply attaching both devices to your computer and clicking “Autofill.” I’m working on an AppleScript that will automate all of these steps for those of you on the Mac side of things, but in the meantime these instructions will get you up and running in well under ten minutes:

1. Launch iTunes. Go to iTunes—>Preferences and click on the “Advanced” tab.
Make sure that the box next to “Copy files to iTunes Music folder when adding to library” is unchecked. If you normally keep this option on, then you’ll simply recheck this preference after we’re done.

2. Connect the iPod that you want to Autofill your iPod Shuffle from.
If it’s name contains any special characters, click on the name of the iPod in iTunes and remove these characters (and while you’re at it, it may be a good idea to remove any spaces from the name). For example, if your iPod’s name is John’s iPod, then change the name to JohnsiPod. If you leave spaces in your iPod’s name make sure to type a before each space in step 5 (i.e., Johns iPod would be Johns iPod).

3. Create a new playlist and name it something like “songs on my ipod.”
Select this new playlist (which should currently be empty).

4. Switch to the Finder / Windows Explorer.
To make things easier, make sure all of your non-application Windows / Finder Windows are closed (Finder—>File (while holding the Option key)—>Close All).

5. Opening the Invisible Folders
Here you have two choices on the Mac: You can either launch the Terminal (found in /Applications/Utilities/) and type the following at the command line:
$open /Volumes/[YOUR IPOD’S NAME]/iPod_Control/Music/F**/
and hit enter, or you can download and run the very simple AppleScript that I wrote and released yesterday to walk you through this step: iPodFolderOpener. Doing this will open all of the invisible folders inside your iPod’s Music folder as Finder Windows. When I did this with my 40GB iPod roughly 70 windows opened up, so be prepared. On Windows, you need to navigate to your iPod via Windows Explorer and enable the view invisible files and folders option and start opening all the folders found within the Music folder (located inside the invisible iPod_Control folder on your iPod). A friend of mine is working on a script to automate this for Windows users, and I’ll let you know when and where (and if) it’s available in the comments to this article.

6. Dragging Files to iTunes
Now, you should have a plethora of Windows open, every single one filled with music files in various formats. Click on the foremost window. Select all of the files contained in the Window (Edit—>Select all). Now simply click and drag all the selected files into iTunes and the playlist you created in Step 3 (which should still be in the main window of iTunes). Exposé (F9) is your friend in this step. After you let go of the files, simply close the Window.

7. Repeat
Repeat step 6 for each of the remaining open windows. Once there are no windows left, move on to step 8.

8. Look at all the aliases
Now—organized nicely in the playlist you created in step 3 and scattered all over your Library—you have aliases (Windoze users know them as shortcuts) to all of the music files on your iPod. Any time your iPod is connected to your computer, they act like any other file in your Music Library: you can play these songs, organize them into playlists, burn them to CD, or right click on a song and choose “Show song file” to open up the window that contains it again for easy drag and drop to another location. Anytime your iPod is disconnected, a grey exclamation point will appear next to the songs and if you try to play one of them, iTunes will ask you if you want to try to locate the song and if you say no, it will ask if you want to remove it. During regular play, iTunes will skip over these missing songs.

9. Click on your iPod Shuffle.
Click on the drop-down menu following “Autofill from:” and select the playlist you created in step 3. Click the “Autofill” button. Wait. You’re done!

This system will work with any iPod. You can even transfer songs from one iPod Shuffle to another. Keep in mind, you can also create playlists based upon the playlist from step 3, and even smart playlists that work solely from the files on your iPod. The only real problem with this system comes when you add songs to the iPod, and then remove them from your computer. Once that happens, you have to repeat the whole process.

This is really a feature that Apple should support. I don’t understand why I cannot move my songs where I want to move them without jumping through such hoops, especially when the iTunes Music Store songs are already protected by DRM. Hopefully soon, either Apple will enable this feature or I’ll have a script completed that will automate this entire process for everyone. Stay tuned and have fun!