My iPod Shuffle can't sync all the music in my playlist at once!

I have a two year old iPod shuffle and starting now, it can't sync all the content at once! It can only sync one song every time I press autofill. I don't want to restore it; it would take a long period of time. Please give me some tips on how to resolve this issue. Thank you!

Make sure that autosync is disabled in iTunes, connect to your new iTunes, right click on it in the device list and choose "transfer purchases" This will copy all apps and bought media to your computer.
After that, right click again, this time choose "backup" to save your app data and other settings.
Make sure to have at least one contact and event set up on your computer before your sync for the first time.
Your ipod will be erased, but you can restore it from the manual backup you made before.
Downloading apps again can be done for free: http://support.apple.com/kb/HT2519
What's inside a backup: http://support.apple.com/kb/HT1766
Transferring data: http://support.apple.com/kb/HT4137

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