Cloud Music Library playlists can only contain songs from your Cloud Music Library.

See Identify cloud status icons in your music library on your Mac or PC - Apple Support. Make sure the track you are trying to add is matched or uploaded.

tt2

I assume when you sy iTunes you mean Music. In the Playlist in Music on your Mac if you hover over the number in the TIME column at the right end side beside the track name. three little dots will appear, click on those and select Add to Library from the drop down menu. After a while it will upload... not that the symbols will give you any obvious clue. You will know it is uploaded when the Add to Library option is no longer there in that menu. Then you can go over the same three dots and choose Add to Playlist from he menu and the select the desired playlist.

I agree that this feature is terribly implemented and totally unintuitive and confusing.

Apple stuff used to be so intuitive and pleasing to use.....

No. If you've removed content from iCloud Music in error then there is no undo or restore method. Neither Apple Music nor iTunes Match should be considered as alternatives to keeping your own backups of your media.

tt2

Thanks. I have 3/4 TB of music which is hard to store internally. I may have lost it in a shuffle over the years. If I find the largest library xls (or whatever) file and make that the library, will they play? Or do I have to find that file on the hard drive and somehow rebut them all on the cloud?

Granddad53 wrote:

Thanks. I have 3/4 TB of music which is hard to store internally. I may have lost it in a shuffle over the years. If I find the largest library xls (or whatever) file and make that the library, will they play? Or do I have to find that file on the hard drive and somehow rebut them all on the cloud?

If you have content stored locally then you can reimport it to the library. If you're an active user of Apple Music or iTunes Match then you cannot simply revert to an older version of your database, as soon as you go online the library will get refreshed with the current state of the iCloud Music Library. There are workarounds, such as going offline before reconnecting to an old library, exporting lists from itm then going back to the current library and importing, or signing out of iCloud Music Library before you go back and then signing in again to merge, but it can all be a bit finickity. If you just want the songs added and you have them then it should be relatively easy to add back into your library. What cannot be done is to restore content that only lived in cloud and was then removed.

tt2

For years I have been paying for cloud storage of my music library, but the one I can access now is not the full version I once had in storage. Can Apple reinstate my largest music library?