On-the-go function stopped working. Suggestions?

Hi, I have an 80 GB Ipod classic, and since I last synced it with my computer, the "on-the-go" function for creating playlists has stopped working. It only works now from the library--in other words, I can add a song from the library, but cannot add a song as it's playing. I tried resetting but this didn't solve the problem. I'm afraid to restore it to factory settings, because, even with backing up, itunes always seems to delete or lose things. Any suggestions? Thanks so much.

Hi, is there any way to make the on-the-go function work in now playing screen? I think this will be more useful when you listen a song and you like it, you can immediately put it in on-the-go list.
Thanks.

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Hi, EJ13.
I see you are having issues with backing up you iPhone and have tried a couple troubleshooting steps. There are a couple more steps I could recommend in the article below.
iOS: Troubleshooting backup issues in iTunes
http://support.apple.com/kb/ts2529
Regards,
Jason H.

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CD Driver DLL 2.1.1.1
Apple Mobile Device 4.0.0.96
Apple Mobile Device Driver 1.57.0.0
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Gracenote MusicID 1.9.3.106
Gracenote Submit 1.9.3.136
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Subnet Mask: 255.255.255.0
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DHCP Server: 192.168.1.1
Lease Obtained: Sun Nov 13 21:09:29 2011
Lease Expires: Mon Nov 14 21:09:29 2011
DNS Servers: 192.168.1.1
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Online: Yes
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Using LAN: Yes
Using Proxy: No
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TLS 1.0 Support: Disabled
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Bruce's iTouch, iPod touch (2nd generation) running firmware version 4.2.1
Serial Number: 1C9053CC201
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On-the-go function stopped working. Suggestions?

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