Sync an MP3 Player with iTunes

Are you using iTunes in Windows, but don't have an iPod? If you have a phone, MP3 device, or most any other handheld that connects via USB to your PC and that appears as external writable media (a drive, in other words) in Windows, then the free iTunes add-on iTunes Agent can automate syncing your (unprotected) iTunes playlists with your handheld. It makes any compatible device appear in iTunes under "My Devices."

"Unprotected" in this case means MP3 files. Only iPods, iPhones, and iTunes know how to handle Apple's "Protected AAC" audio files, but most any current handheld device is going to have an MP3 player. Apple, in fact, has recently given up on protected file formats, but if you have older purchased music that you want to play on your phone or MP3 player, you're going to need to convert that protected music to unprotected MP3 format.

I used TuneBite (reviewed here) to convert my purchased, protected AAC tracks to good-quality MP3 tracks.

iTunes Agent is a 334 kb download. Since it's a plug-in, it is not very large.

Installation is very straight-forward. First it shows the installation notes, then the license agreement, then the installation folder location. The actual installation took under a minute.

iTunes Agent runs in the notifications area (ie, system tray) in Windows. An important first step is to tell it about the devices that you want to use with it. Again, these must be devices that appear as removable storage when plugged into a USB port.

I used a Palm LifeDrive for testing. This is an older handheld device that has a 4-GB microdrive for storage. When "Drive Mode" is selected, it shows up as removable storage in Windows Explorer under "Computer."

Upon first start, iTunes Agent puts up a "Configure Me" panel in which it said that it needed to "configure myself for this new version." This was worth a chuckle. It's nice to see that the programmers don't take themselves too seriously.

After it finishes configuring itself, click on the iTunes Agent icon and select "Preferences." It will immediately warn you that any music in the "Music" folder on the device will be deleted when the device is synchronized with the iTunes playlist. This, then, would be a good time to back up your existing MP3 music, which can be as easy as copy/pasting the Music folder to your desktop for safe keeping.

So I emptied the Music folder.

Then I clicked the icon and selected "Preferences." This dialog then opened.

To add a device to be monitored, click the "New" button. The dialog then shows the following entry fields:

Name: This is the name of the device as you wish it to appear in iTunes.

Synchronization pattern: The three choices are iTunes, Artist Folder, and Flat. I left it on iTunes, but if you like the shortest presentation of your track titles, choose Flat.

Music folder: This is the folder the tracks are to be put in on the handheld device. On my Palm, the actual path to the folder was N:/Music. iTunes Agent looks first for an identifier and then the path to the music folder when it starts to sync. The easiest way to set this folder is to hook up the device so that it appears in Windows Explorer and then click "Choose" in iTunes Agent and actually navigate to the folder you want to use. Again, "Music" is the default. If you leave this blank, iTunes Agent will dump your tracks on the root directory of the device.

Recognize by folder/file: This is the identifier that iTunes Agent looks for. Depending on the device, it will be either a file or a folder. To set this up, click "Create" and navigate to the root directory of the device.

Associate with playlist: Leave this at the default of "Use device name" if you want your handheld to appear to appear in iTunes under "My Devices." You can also click the droplist and select any other playlist folder in iTunes.

When done, click "Save" to create your device's folder under Playlists.

Next: Using iTunes Agent, Setting Up and Trying a Sync, Wrapping Up, and Related Reading