Music files deleted from hard drive and iTunes library

Often, after iTunes software updates, I find that some of my music files that have been uploaded from cds are completely erased from my music library and from my external hard drive, where I keep all my music. I always make sure I turn on the external drive before opening iTunes, and I quit iTunes before turning off the external drive.
So why is my music disappearing?! Where does it go? This has been a problem for a long time and I can't find any solutions online. Please help! Thank you!

When you have the unit in the dock, anytime you sync, you have to make sure that it will sync again to the folder. If it isn't set to sync the same folder where you had the music sync before, it'll delete the file.
That's just the way it's set up. So you have be conscious of it.

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