Why can’t I transfer some songs from iTunes to my iPod?

31 May 2012
Windows 7
Explorer 9
31 May 2012 | Windows 7 | Explorer 9

After restoring my iPod, I get a message on some songs that says: “iTunes could not copy the file ‘name of song’ because the file could not be found.” Some of the downloaded songs from iTunes are not showing up under the directory “iTunes music.” Those songs downloaded or imported from CDs are in my playlist and can be played on my computer, but can’t be transferred to my iPod.

I also had to get another hard drive because of what could have been a virus attack or just a failure, so I restored some of the files from a backup DVD and some were downloaded from Apple’s server with the assistance of a tech support rep. A lot of CDs had to be re-imported. The error shows up on imported and downloaded songs from iTunes. To fix it iTunes support wants $59.00 which I think is a rip-off. Does anyone out there know how to fix these problems?

I’ve seen some answers posted on here about this but the answers aren’t very clear and concise. The details are kind of sketchy or not 100% applicable to my situation. I love my iPod and have hundreds of dollars worth of downloaded songs but this is very frustrating and disappointing to say the least.

Some real help would be greatly appreciated!

tl;dr – I can’t drag some files from my iTunes on my desktop PC to my iPod after doing a restore. The songs are in my playlist and play on the computer fine but some I can’t put back on my device because I get a message that says the file can’t be located. Sure enough, they aren’t showing up in the iTunes music folder. Why weren’t they restored?

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