I had the same problem and I have now sucessfully fixed it! I have an iPod Nano which works perfectly and I bought a new 2nd generation Shuffle for my son. I could not get any music to synch to it or update the software. I followed the advice in the attached link and everything now works. Make sure you run your scan disk in your antivirus software after adding the .bat file and before attempting to connect to iTunes and synch to your iPod. Restore your iPod - the new software should load if necessary and then you should be able to synch. Good luck! http://www.info.apple.com/kbnum/n304996
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You just need to import your songs into iTunes library, then make a playlist with the songs, connect your iPod to computer, iTunes will detect the iPod automatically, then click iTunes menu "File -> Sync iPod", the songs will be transferred from iTunes to iPod. Or You may try this ipod transfer, it's
a nice iTunes alternative that can help you manage iPod files including delete,
upload, play, copy, etc. It's much easier to use than iTunes.
How Do I Download Songs Onto My iPod Nano? IPod Nanos are portable multimedia players that allow you to playback songs and other content (e.g. video) no matter where you go. They come in a variety of memory sizes such as 4GB or 16GB (gigabytes) and work with iTunes to upload songs. ITunes is the iPod default management program which allows you to upload songs to its library, create playlists and sync music on your iPod quickly and easily. This simple process will have you jamming to your favorite songs in no time.
Downloading to an iPod Nano1Connect your iPod Nano to the computer using the USB cable. Launch iTunes if does not automatically launch. When you launch iTunes, it will display your iPod Nano on the left panel. 2Add music to your iTunes library. Click the "File" button on the top menu and click "Add to Library." Locate the song you want to upload to your player and click "Open" to load it to your program. 3Click the "+" button on the lower left panel to create a playlist. Type a name for the playlist and drag the uploaded file to it. To upload additional songs, repeat Step 2 and drag the uploaded additional songs to the created playlist. 4Drag the songs in the playlist up or down to select the order in which the songs will play. 5Sync your iPod Nano. Click the iPod icon on the left panel after importing songs and adding them to the created playlist. Click the "Music" tab and click "Sync music." Click "Select playlists, artists and genres" and select the playlist you created that contains the songs you want to upload. Click "Apply" to automatically sync and download the songs to your iPod Nano. 6Click the "Eject" button and disconnect your iPod from the computer.
Tips & Warnings Click "Music Store" if you want to purchase a music file. Search for the song on the iTunes store and download it to the iTunes library.
You just need to import your songs into iTunes library, then make a playlist with the songs, connect your iPod to computer, iTunes will detect the iPod automatically, then click iTunes menu "File -> Sync iPod", the songs will be transferred from iTunes to iPod.
If iTunes not works for you, You may try this ipod transfer, it's a nice iTunes alternative that can help you manage iPod files including delete, upload, play, copy, etc. It's much easier to use than iTunes.
There are some mp3 songs that you can add to the iTunes Library but not to the iPod
This is a format issue i believe
if this its your case you should try to get again the mp3 or burn it from th CD again an then try to upload to the iPod
Best way to transfer music on the ipod is through iTunes. Apple uses its own mechanism to copy music, pictures and videos on the device and traditional methods such as copy/paste and transfer from windows media player, winamp, etc do not work.
download itunes from www.apple.com/itunes
Are you running the most current version of iTunes? If not try upgrading. After that, try seeing if there is an firmware upgrade. If there is, try upgrading that too. Then try reuploading songs. If it is still not working, it might be damaged or just not working anymore. Only use Itunes when uploading songs to ipod regardless of type.
When you try to sync files to any iPod in iTunes on a Mac or Windows computer, you might see the following -69 error message: "Attempting to copy to the disk failed. An unknown error occurred (-69)"This error occurs when iTunes tries to send files to your iPod, but a file (or files) is unusable (something is wrong with it).
To figure out which file (or files) is causing the error, update to the latest version of iTunes and then do this:
Control-click (Mac) or right-click (Windows) on your iPod icon in the iTunes Source pane, then choose Sync Songs from the shortcut menu.
Watch the display at the top of the iTunes window while your iPod is being updated. The name of the problematic file should appear in the display right before the error appears.Then remove the bad file from the list of songs to be synced to your iPod:
Select the iPod in the iTunes Source pane.
Click the Settings tab.
Select the "Only sync checked items" checkbox (please note that this checkbox is only available for an iPod configured to update automatically).
Select the appropriate item under Library in the sidebar and find the bad file in the list. (For example, if the file in question was a song you would select Music in the iTunes Source pane. If it were a video you would select Movies or TV Shows in the sidebar.)
Deselect the checkbox next to the file name.
Repeat steps 1 and 2 to update your iPod. If you have multiple problematic files in your iTunes library, you may need to repeat the other steps to remove them too.
To prevent future issues, you should delete the unusable files from your iTunes library, then restore them from a backup or reimport them from a CD.
If you're not able to isolate to any single file or if another iPod works with the same songs, then disconnect any other devices connected to USB or FireWire and try again. If the issue continues, then then try resetting your iPod. If the issue continues, then restore your iPod.