Organising my music in iTunes

I have just painstakingly moved all my music from a laptop to my desktop using an external hard drive.

All the music is from my own CDs which I have added to iTunes as I buy them.

The music is there in iTunes on my Desktop, but I prefer to use my own playlist method of storing for ease of use on my iPod.

My problem is that now I cannot move the music into the playlists that I have created in iTunes - neither by dragging to the side bar nor right clicking on the album and going down the playlist list.

It seems to me that my playlist list is "dead"

Any good ideas how I can revive it please?

iPod Classic

Posted on Feb 25, 2020 10:53 AM

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Posted on Feb 27, 2020 11:46 AM

It sounds like you moved the song file after you added the song to iTunes. Try this:


Right click on a song that gives this error and select "Song Info". Then select the File tab. At the bottom of the window, you will see the location where iTunes expects the song file to be.


At this point you can do one of two things: either move the song file back to the location shown in the Song Info > File tab, or else find the file using Windows File Explorer, and then provide this location when iTunes ask where to find the file.


By the way, you can change the way that iTunes sorts songs in the Song Info > Sorting tab.

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Feb 27, 2020 11:46 AM in response to Totterrockchick

It sounds like you moved the song file after you added the song to iTunes. Try this:


Right click on a song that gives this error and select "Song Info". Then select the File tab. At the bottom of the window, you will see the location where iTunes expects the song file to be.


At this point you can do one of two things: either move the song file back to the location shown in the Song Info > File tab, or else find the file using Windows File Explorer, and then provide this location when iTunes ask where to find the file.


By the way, you can change the way that iTunes sorts songs in the Song Info > Sorting tab.

Feb 27, 2020 11:47 AM in response to Totterrockchick

I'm glad you elaborated.


That's why the songs won't go into the Playlists then. My guess is that you pointed iTunes to the external drive and effectively told iTunes to use those files (in that location). Now that the external drive isn't there (or it has another drive letter assigned to it), iTunes can no longer find the files (the song-files).


There's an important distinction between a song and a file (or song-file)

  • the song is what you hear
  • the file is what iTunes uses to play the song for you

They are the same thing; it's just that when you ask iTunes to play a particular song, it looks outside of iTunes (and onto your computer) for the file as the source of that song. What you work with, inside iTunes, when you ask it to play a song, or when you edit the song in some way, is the song.


You may need to read through the rest of this post a few times first, before trying to do it, to make sure you've understood what I'm suggesting. Once you do, actually doing it should be easier.


What you needed to do was copy the songs to your computer and then add them to your iTunes Library.


Think of it like this:

when you add a song to your iTunes Library, what you are actually doing is telling iTunes where to find that song and all iTunes does is list it. The songs are listed inside of iTunes, but the files are outside iTunes. So in other words, iTunes is a database, that knows where the songs are. If the file is then moved, renamed or deleted, or the drive is no longer connected, it cannot play the song. Hence the message you get.


At this point you may be thinking "why doesn't Apple make all this clear?"


It's a good question (even though I asked it). Unfortunately, I think computer programmers' minds just don't work in the same way as the rest of us. (That's not a compliment.)


So - hopefully, you still have access to the hard drive that had the old songs it (or the old computer). You obviously need access to them. Read through the next points and decide which method you want to use to resolve this issue. You have two options (well, plus a fallback, just in case):

  1. leave the music on the external drive and keep it connected to your computer. If you're lucky (really lucky) all you then need to do is try and play the songs. As long the songs have the same filepath as they did when you first told iTunes about them, all you would need to do is play the song - and iTunes will find it. The next two sub-points are very important:
    1. With this method, that external drive will have to be connected to your computer and ready to read before you start up iTunes. That's every time
    2. The drive will also have to have the same drive letter every time. You may wish to use this method if you're short of storage on your computer
  2. alternatively, you may wish to copy the files from the external drive, onto your computer and then tell iTunes where to find those files. You would do this by trying to play a song and when it fails, you then tell iTunes where to find it now. If you manage to do this correctly, iTunes would then look in the same filepath for any other missing music and sort out the missing ones by itself


The "fallback" option is to:

  • delete the old non-working entries in iTunes
  • then use either of the above methods to add the music to iTunes. You would do that by using the command File/Add folder to Library and then navigate to the master folder where the music is located. Don't forget to take into account whether you have copied the music to the computer, or whether you're telling iTunes to use an external drive.


You could try with a couple of songs and see how you get on. Once you understand the process, it should be far easier to do for the rest of your Library.

Feb 26, 2020 11:30 AM in response to Totterrockchick

You can only manually add songs to Regular Playlists. You cannot drag songs to Smart Playlists, or to Playlist Folders.


Here's a screenshot, showing the icons for the two Playlists types and the Folder that I've mentioned:



You can add both Regular Playlists and Smart Playlists to Playlist Folders, but you cannot add songs directly to the folder. Smart Playlist have songs added automatcially by iTunes, acordin g to the rules that you choose and specifiy for that specific Playlist.


If that does not address your issue, please expalin a bit more about what you mean by

... I prefer to use my own playlist method of storing for ease of use on my iPod.

... since I don't understand what you mean. What is a playlist method?

Feb 26, 2020 3:49 PM in response to the fiend

Thank you very much for your reply.

What I mean is that I don't like my music simply being in iTunes - I like everything strictly alphabetical by surname e.g. David Bowie would be found under D just on iTunes, but my playlist would ensure he was under B i.e. Bowie David.

It is the regular Playlists that I cannot move the music into. I can see all the music is in iTunes (198 GB) but when I try to drag and drop the album it doesn't "spark" the Playlist.

The Playlists seems OK as I have successfully imported CDs and THEN dragged them into the Playlist. What I cannot do is move around any of the tunes I moved from the laptop to the desktop - could I have corrupted them somehow ?

It seems to me it is a software problem and I wondered if my laptop was using an earlier version of iTunes, while I have the latest version on my desktop - would that make any difference?

Any help you can give would be much appreciated as I don't fancy having to import all my CDs again!!!

Feb 27, 2020 8:49 AM in response to Totterrockchick

Totterrockchick wrote:

It seems to me it is a software problem and I wondered if my laptop was using an earlier version of iTunes, while I have the latest version on my desktop - would that make any difference?

I doubt that it's a software issue and no, I don't think it would make any difference.


If I understand you correctly, you're only having issues with music transferred from one computer to another. If so, the first question is; do the problem songs actually play in your desktop?

Feb 28, 2020 2:30 AM in response to the fiend

That makes an awful lot of sense and I can't wait to try it out! However, I want to take the time to proceed cautiously, so must wait until Sunday when I have a whole day I can play...

Naturally, I will let you know how I get on, but whatever the outcome, I cannot thank you enough for the great amount of detail and help (not to mention your time) that you have given me. You are a star! x

Feb 28, 2020 10:46 AM in response to Totterrockchick

I was so keen to try out your suggestion that I did a little test run tonight and EUREKA!!!! it worked...

I am downloading the files from the laptop to an external hard drive and then importing them into the C drive of my PC and from there into iTunes where not only can I play them but I can also move them into my playlists...

You have made an aged rock/blues fan very happy....x

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Organising my music in iTunes

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