If your iPod is set to transfer music manually, then you will always need to manually eject the iPod. See:
How to Transfer Music Between the Computer and iPod
If you are in auto mode (full or selected playlists), then this may help:
Here are several ways to
Manually Eject your iPod
And:
How to Safely Disconnect
Other ways in addition to the above links are:
--- Eject the iPod using the System tray "Safely Remove Hardware" icon. This icon looks like a small gray rectangle with a green arrow floating above it. It is only there when a removable device (like the iPod in this case) is attached to the computer. Right-click & select 'Safely remove..', then click 'Stop' in the next window, OK in the next window, and then Close to complete the ejection.
---
Reset your iPod, then disconnect when you see the Apple logo.
--- Hold ‘Ctrl-Alt-Del’ to bring up the Windows Task Manager. Go to the Processes tab and look for iTunesHelper.exe and iPodService.exe. Select each of them and hit the End Process button. Close the Task Manager Window and try ejecting the iPod via the safely remove hardware method above.
--- If you are still having problems you can try one more thing. Right-Click on the My Computer icon and select ‘Manage’ from the list of actions. Go to the Services and Applications item and from there the services item. Double click on the services item to bring up the list of services currently installed on your computer. Look for the iPod Service and double click on it. From the new window select Stop. Now try again to eject using the safely remove hardware option above.
--- If all of the above does not work, power down the PC and then remove the iPod.
After ejecting the iPod, try
Resetting Your iPod to clear the issue.
