My music is deleting when I try to play it!!!

Question

I recently restored my iPod(Black 5th gen), losing all the music I had lost when my computer crashed. The problem was that iTunes no longer wanted to recognise my iPod and none of the songs were showing up either in iTunes or on the iPod itself.
Since I restored it and installed the latest software updates, now when I try to play a song from my iPod in iTunes, it more often deletes the song rather than plays it. I thought I was going crazy until it happened several more times.
Has this happened to anyone else and if so is there any way to fix it?
(I have since found that winamp was used to put some of the songs on my ipod, could this have any effect on it?)

Answer 1

Maddie1016
You have quoted me out of context (and not made it obvious that you are quoting) and perhaps ignored my use of the phrase _the next time you have a failure_ . By failure, I mean a computer failure which results in restoring the iTunes Library.
The thing is... it does work! If you manage to find a missing song and tell iTunes where it is, it will still be there next time iTunes looks for it, whether it's in the iTunes music folder or elsewhere.
However!
Suppose you have songs on an external drive/hard disk, memory key/stick or similar and you tell iTunes that is where they are located. Those songs must be in the same place the next time you start up iTunes. In other words, the drive must have the same letter.
Take as an example: you turn on your computer and then turn on the external hard drive (with some of your iTunes Library songs on it). The external hard drive will be allocated the next letter in the alphabet. (My next letter is F:) Then you plug in a memory key. The key will now be allocated the next letter in the alphabet, in my example it will be G. When you finish, you close down your computer.
*The next time you start your computer* you forget to turn on the hard drive, but instead you connect up a camera and transfer pictures from the camera to your computer. The camera will have been allocated the letter F (as in my example). The next thing you do is connect the memory key, which will be allocated drive letter G, (the same as previously). Only then do you remember that you have not turned on the external hard drive, and you do that now. It will be allocated the drive letter H. You then (safely disconnect) the camera and then start iTunes.
iTunes will still find songs on the memory key (becasue it has the same drive letter as before) but it will not find songs on your external hard drive _because it now has a different drive letter_ and therefore the songs are in a different location.
In my previous post I suggested that there is another option which required a bit more work. That is, once you find the missing songs, to move them to the iTunes Music folder. To do this:
Look in the iTunes Music folder, in Windows it is: *My Music/iTunes/iTunes Music* unless you specified somewhere else. In there:
*For a new artist,* create a folder with the artist name and then go into that;
*For an existing artist,* find and go into that artist's folder;
*For a compilation album,* find and go into the Compilations folder.
In each case, once you are in the correct folder, create another folder with the album name. Place the songs in the new <album name> folder.
As you can see, it's a fair bit of work, and to keep it readable, I omitted it from the original post but said I would supply it if requested.
Lastly:
v4nitee wrote:
now when I try to play a song from my iPod in iTunes, it more often deletes the song rather than plays it.
Has any of this information helped you? Your feedback would be appreciated.