How to transfer music from your iPod to iTunes/your computer.

1. First you need to connect the iPod without iTunes doing the auto-sync. 

• Hold down the Shift and Ctrl keys while connecting the iPod to your computer.
• Don't let go of Shift+Ctrl.
• If iTunes doesn't open automatically open after connecting the iPod, open iTunes.
• Don't let go of Shift+Ctrl.
• Wait until the iPod comes up in the Source list under DEVICES (it may take a while, but don't let go of Shift+Ctrl)

• From the Desktop, go to My Computer and click once (or select/highlight) on the iPod, (usually drive E:, F: or G:).
  
  
• Go to Tools > Folder Options.
  
  
  
• Click View tab > scroll to Show Hidden Files and Folders and select it. Click OK.
  
  
• Look in the iPod drive, and find a folder called iPod_Control and open it.
  
  
  
• You'll see the Music folder. In it will be folders and files named F00, F01 and so on.
  
  
  Note: To see the original name of the song/file, just mouse over it.
  
  • If you need all the contents of the iPod on you computer, copy the whole Music folder. 
  • If you only need some of the files, look through the Fxx folders until you find the files you want and copy.
    
  • To copy:
    
    • Click once on the folder or hold down the Ctrl button and click once on each of the folders you want.
    • Go to the Edit menu and select copy.
    • Minimize all windows, right click over a blank area of the desktop, select New > Folder (name it Songs).
    • Right click over the Songs folder and select Paste.
      
      • Depending on the number of songs, this may take a long time to complete.
  
  
  Note: All the hidden files that are on your iPod are playable on iTunes once you transfer them to your computer's iTunes.

• Open iTunes (if needed) and go to File > Add Folder to Library.
  
  
• Select the folder you want to import and click OK.
  
  
  • This also may take awhile to complete.
    

Zolved Tips:

• If you think you'll be doing this a lot, you should look into two things:
  1. Back up your iTunes library to an external hard drive periodically.
  2. Use an "iPod management software" other than iTunes.  See this comparison of iPod managers on Wikipedia.
• You might want to set iTunes to manually manage your iPod.  This will mean you will have to drag-n-drop new stuff onto the iPod yourself.
• Depending on which iPod model you have, the iPod may get very hot during the copying process.