(http://www NULL.rj-diamond NULL.com/alex/wp-content/uploads/2009/10/apple NULL.jpg) One of the questions I did receive this week involves not being able to add new music (either from the iTunes store or from CD) to an iPod. 

     I didn’t get to many details on what version of iTunes or what kind of iPod or if this was Windows or Mac, which made this answer a little difficult.  Using the idea that it involves a new(or newer) version of iTunes, and taking a stab at it based on previous history with iTunes, here is what I think for both Windows and Mac. (**If this is not correct, I just ask the person who sent in the initial question to send me a follow up message with as much detail as possible and I’ll see what I can do).

In Windows:

    Sometimes the iTunes updater does not properly update.  The updater is supposed to update the version on your pc and then update iTunes on your iPod, however, sometimes if you disconnect your iPod before the update is complete or if the PC froze or any of a 1000 “Acts of Nature” occurred, then it could be that your iPod never got its part of the update. 

So this is what you do –

• From your PC – Open My computer –> The on the address bar on top type c:\Documents and Settings\All Users\Application Data\Apple\Installer Cache.  If you typed it correctly you should end up with a page that looks similar to the picture below.

(http://www NULL.rj-diamond NULL.com/alex/wp-content/uploads/2009/10/softwareupdate1 NULL.jpg)  The reason you will type this in is that by default in Windows the Application Data folder is considered a hidden folder and you wont find it unless you unhide your folders in Windows.

• Within this Installer Cache folder you may see more than one  Apple Software Update folder, if that is the case select the folder with the highest number (2.1.1.116 is the number in my case) or the newest folder if you are looking at the window via details view

(http://www NULL.rj-diamond NULL.com/alex/wp-content/uploads/2009/10/applefix2 NULL.jpg)                                              

• Now double click on the file marked AppleSoftwareUpdate.msi.

(http://www NULL.rj-diamond NULL.com/alex/wp-content/uploads/2009/10/applefix3 NULL.jpg)

• You will now see the Repair function, select that and the system will reinstall the update you selected.

(http://www NULL.rj-diamond NULL.com/alex/wp-content/uploads/2009/10/applefix4 NULL.jpg)

• Once that update is completed.  Click on finish, and try again, and that should correct the issue.  

From a Mac:

This is from Apple Support (http://support.apple.com/kb/TS1461 (http://support NULL.apple NULL.com/kb/TS1461))

Certain models of single processor Power Macintosh G5 computers may show iPod nano mounted in the Finder but not recognized in iTunes. If this happens to you, try restarting your computer and Setting Energy Saver to highest performance and turn off hard disk sleep. If you have an iPod nano, but don’t have a G5, then follow the other steps below.

Mac OS X 10.5.x

1. Insert your Mac OS X 10.5 install disc.
2. Open the "Optional Installs" folder.
3. Double-click Optional Installs.mpkg.
4. On the Custom Install window of the Installer, select the option to install iPod Support.

Mac OS X 10.4.x

Install the latest available Mac OS X 10.4.x update. If you are already using the latest version of Mac OS X 10.4, or if updating does not help, perform an archive installation (http://www NULL.info NULL.apple NULL.com/kbnum/n107120) of Mac OS X 10.4.

Mac OS X 10.3.x

1. Navigate to /System/Library/Extensions.
2. Drag the iPodDriver.kext file to the Trash (you will be required to enter an administrator account password).
3. Download and install the Mac OS X Combined Update 10.3.9 (http://www NULL.apple NULL.com/support/downloads/macosxcombinedupdate1039 NULL.html).
4. Restart the computer when prompted to do so by the installer.
5. Connect the iPod.

Mac OS X 10.2.8 and earlier
To resolve this issue with earlier versions of Mac OS X, you’ll need to delete one file and reinstall iTunes. Follow each of the steps below.

Step 1
Delete the file using Terminal

Warning: The steps below describe how to remove a file by entering commands in the Terminal application (located in the Utilities folder inside of the Applications folder). Users unfamiliar with Terminal and UNIX-like environments should proceed with caution. The entry of incorrect commands may result in data loss or unusable system software.

1. Open Terminal (/Applications/Utilities).
2. Type: sudo rm -R /System/Library/Extensions/iPodDriver.kext
3. Press Return.
4. Enter the administrator account password when prompted.
5. Quit Terminal.
6. Restart the computer (From the Apple menu, choose Restart).

Step 2
Reinstall iTunes

1. Download the latest version of iTunes from the iTunes download page (http://www NULL.apple NULL.com/itunes/download).
2. Install iTunes.
3. Restart the computer after the installation has completed.
4. Connect iPod.

Step 3
Delete the iPod.plist file

Remove the following file in the your home directory and open iTunes again.
~/Library/Preferences/com.apple.ipod.plist\

*****As always I am just making suggestions based on information give.  If the information I receive is incomplete, the suggestion my not work.  It is up to you to make sure you take backup your software (or files or Music) before trying any repair solutions, in case a restore is required.