Ipod wont update new songs

when i plug my ipod into the computer so it can charge and update in my new songs, it stays on the "do not disconnect" screen and doesn't update it anymore.
help?
ipod mini

iTunes prefs -> iPod.
Change to Auto update.

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Have you successfully synced from this iTunes library/computer before?
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So, if you select one of these songs on the iPods screen, and try to play it, what happens? The iPod does nothing? It skips to the next song?
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My ipod will not update new songs from itunes. I've purchased several songs from the music store, updated my playlists and as added some from my CD collection and they are not transfering from my library to my ipod.
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Thank you for responding.
Doesn't it have to be on either manual or auto update? What other option is there?
I will try downloading latest updates.
I know it will work if I reset it (have done it a few times already). I just hate having to restore factory settings everytime I want to put a new song onthe ipod.

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iGadget Windows Only
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Hello All,
I think I came up with a work around by accident and didn't realize it until I read this post.
Did all the same stuff most have done, reset to factory, reapplied the updates, etc, still not enough free space, even though there was plenty before.
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https://www.apple.com/support/ipod/five_rs/
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Help ipod wont update songs!!!

my ipod and itunes are updated and i tried to update my ipod with newly downloaded songs from i tunes. it says do not disconnect and the little ipod thing comes up in itunes and updates the 158 songsor w/e. then i go to play them on my ipod but they arent there! they r inthe ipod file in itunes but not actually on my ipod! what do i do! ive spent hours on this helpppp.

I have been experiencing the same issues with my Ipod. A week ago my Ipod started to act up. I reset my Ipod and it showed the unhappy face icon. I plugged it into my computer and by the morning it was fixed. Today, however, I tried to update the songs on my Ipod. After updating Itunes said my ipod contained 2993 songs. I disconnected my Ipod an checked the settings:About and it said 2909 songs. I understand how frustrating this is and I wanted you to know that your not alone in this endevor. I also tried the above solutions but none succeed to solve the problem. Hopefully a solution will be brought to our attention soon.

HT1386 ipod syncs but doesnt update new songs from the library to the ipod

I had problems syncing my ipod touch, a message appeared on the computer, which said the itunes program was corrupted/damaged so it advised to reinstall itunes, which i did. This wiped my library from the computer. When i connected the ipod to the computer it said it is was syncing, but no data got transfered either from the ipod to the computer or visa versa. My ipod still retains its songs/apps etc.

See also Recover your iTunes library from your iPod or iOS device.
tt2

Ipod wont update new songs

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