itunes – Is there an efficient fix to the computer not authourised loop for many songs in a library?

I have seen variations of this question, but the scope of those questions are both limited and non-preventative.

I have the commonly reported problem of, when I go to play some songs in my iTunes library, iTunes will ask me to authourise my computer. When I input my password, it tells me I am already authourised and then asks me to authourise again.

I know the fix for this: remove the download and redownload the song. That’s fine. However the issue is that large amounts of my library are now like this. I did attempt to delete my whole library and redownload, however this simply lead to other songs being afflicted. From what I can tell I don’t know how to pick out the songs with this issue, and so I would have to sort through my nearly 1500 tracks, and examine each one.

I’m lazy. I don’t want to do that (I will if there is no other way however.) Is there a way I can either:

  • Select all of these songs, remove their download, and redownload them.
  • Prevent iTunes from throwing this in the first place so I can delete and redownload everything without having to worry about different songs being afflicted. (Though the preventative measure would be useful either way)

For some extra context this did start when I moved my iTunes library to my external hard drive, as I don’t have the space on my laptop’s hard drive to store my entire library. I can’t think why this would pose an issue? I believe iTunes is installed on my C Drive, so perhaps them being on different drives is causing a problem.

If I were just playing these on my computer, I wouldn’t be worried, as I could simply sort them as they crop up, however I use an iPod and this problem prevents songs playing on that as well.