Problem syncing songs on 5th gen 30 GB ipod

My brother recently got an ipod nano and we began using both (my fifth gen) with iTunes on one computer. It worked fine the first day but after that it won't work. When i connect either ipod it works but then when i drag songs to them, the songs doesn't go on. Finally when i try to disconnect, it won't let me. I have to disconnect it via My Computer. Can Anyone Help Me!!!!!

Check your update settings. Connect your iPod and click on it's icon in the iTunes source list (the narrow pane on the left). This will bring up the preferences tabs in the main pane on the right. The first tab you'll see is Summary, look for "manually manage songs and videos". To be able to drag songs from the library to the iPod there has to be a check mark against that option: Managing content manually on iPod
Something to remember about using an iPod in manual mode is that it automatically enables the iPod for disk mode. When and iPod is enabled for disk mode the "Do Not Disconnect" message will remain on the display until you physically eject the device. In that case use the Safely Remove Hardware icon in the Windows system tray on the desktop and check this link for alternative methods:: Safely Disconnect IPod
If the iPod is set to manual and your problem with dragging persists try restoring your iPod. Just be aware that restoring will erase the iPod's hard drive, reload the software and put it back to default settings, so if you have songs on your iPod that aren't on iTunes you will lose them if you have no back up. Once the restore is complete follow the on screen instructions and it should connect to iTunes and give you a prompt to automatically update your library onto the fresh installation. If you want to update manually or using selected playlists choose no and it will default to manual mode and you can choose whatever setting you like: Restoring iPod to factory settings with iTunes 7

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