Transferring library to new 3rd gen ipod

I naively assumed that it would be simple and automatic to transfer my entire library to my new 3rd gen ipod. In fact fewer than 25% of the songs have transferred and the rest 'could not be found.' I have updated to the most recent version of itunes. Has anyone else had this problem with a new ipod? And is there a solution?

i have a similar problem!
my songs from my old itune library wont sync to my new ipod and they are different generations.
we both need answers here!

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    Only if something goes astray, which happens some times.
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  • Extended Start-up Time in 3rd Gen iPod

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    Macs can read Windows formatting so you just need to connect your iPod to start using the iTunes library. However if your iPod is set to update automatically take care when connecting back to your new computer and a different iTunes. If it is set to automatically update you will get a message that your iPod is linked to a different library and asking if you want to link to this one and replace all your songs etc, press *No* (or "Cancel" if you are using iTunes 7). Pressing "Yes" (or Erase and Sync in iTunes 7) will irretrievably remove all songs from your iPod. Your iPod should appear in the iTunes source list from where you can change the update setting to manual and use your iPod without the risk of accidentally erasing it. In iTunes 7 Check the "manually manage music and videos" box in Summary then press the Apply button. Don't uncheck Sync Music it will be unchecked by default when you choose the manual setting: Managing content manually on iPod
    You can also use a keyboard command to prevent your iPod auto-syncing with iTunes. While connecting the iPod to the computer on a Mac hold down the Option and Command (⌥ and ⌘) keys, (on Windows hold down the Shift + Ctrl keys). This will stop the iPod from auto-syncing with iTunes and the iPod will appear in the source list. Wait until you are sure the iPod has mounted, and that it will not auto sync and then you can let the keys go. This may take between 20 to 30 seconds depending on your computer.
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    See
    iOS: Device not recognized in iTunes for Windows
    - I would start with
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    Also see:
    iPod not recognised by windows iTunes
    Troubleshooting issues with iTunes for Windows updates
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