moving iTunes Media files

I know it is really OCD of me, but if I look in iTunes > Preferences > Advanced at the media path it doesn't put spaces around the slashes.

There are also two possible layouts for the library:

• <Media Folder>/<Artist>/<Album>/[D-]##<Name>.<Ext>
• <Media Folder>/Music/<Artist>/<Album>/[D-]##<Name>.<Ext>

Which one you have depends on a hidden preference file. Again, see Managing your Mac media libraries - Apple Community and the section on iTunes Media Organization for details. The media folder path could include a terminal /Music and the library be in the first layout, or the path doesn't include the final /Music but the library is in the second layout. You may also want to explicitly avoid adding the last /Music folder when rearranging things with the Music app as it seems somewhat redundant.

From your description it isn't clear what the exact value under iTunes > Preferences > Advanced is. Or indeed if you're talking about iTunes when in fact you're running Music under Catalina or later and we should be talking about Music > Preferences > Files when looking for the media folder setting.

Macs have this great feature that, as a rule, you can normally move files from one place to another within the same volume and whatever software has references to those files it will still be able to find them. This means that you can usually manually rearrange content the way that you want to without breaking things. That said, ideally you would let iTunes/Music take care of moving the files and updating its references so that you can be certain nothing gets broken. You mentioned that you thought your paths had too many nested folders. There are two options here. One is to choose a new media folder anywhere, and then consolidate to that folder. This makes copies of everything, which takes time, and if your library is larger than the available free space will fail. After consolidating you have to manually clean up the original files. The alternative is to choose a new media folder at a higher level within the existing path. E.g if the current path is .../Apple Music Library/Music/Media/Music you could pick any of the following to be the new media folder.

.../Apple Music Library/Music/Media

.../Apple Music Library/Music

.../Apple Music Library

Once the new folder has been picked if you turn Keep organized off, and then back on again, the files will be moved to new locations within the current media folder, so no new copies are created, which is a much faster process, and doesn't require further manual housekeeping. Because this is a Mac you could also potentially change the name of the top level folder as a separate action at some point. In either case it is a good move to backup your iTunes or Music library files before making changes.

tt2

You can move files up the existing tree by picking a higher level folder to be the media folder and then turning Keep organized off and on again. It would be useful to know what the official path to the media folder is now. I'm going to guess .../Dropbox/Music Library/Music/Media, with iTunes adding in the /Music before the <Artist> folders because of iTunes Media Organization. If so you could, for example, select .../Dropbox/Music Library/ as the media folder, and have iTunes pop all the files up a couple of nested folders without having to create copies internally. Of course Dropbox is still going to take hours to process the changes.

tt2

As above the Copy files option only applies to newly added content that is located outside of the designated media folder when you add it to the library.

Choosing a new media folder location may prompt you to consolidate the library to this new path, or you may need to consolidate manually using File > Library > Organize Library > Consolidate Files. When you do so any file located outside of the media folder will be copied into it, using the standard iTunes/Music layout of artist and album folders.

tt2

I don't know if you did anything wrong or not. It could be the interaction with Dropbox is slowing things down.

tt2

See Managing your Mac media libraries - Apple Community and in particular the section on iTunes Media Organization. Note that neither iTunes nor Music are guaranteed to play nicely with third party cloud syncing software. Apple have Apple Music or iTunes Match to sell to you.

tt2

Keep organized... tells the library it can rearrange files and folders inside the media folder to match the standard iTunes/Music layout of <Media Folder>[/Music]/<Artist>/<Album>/[D-]## <Name>.<Ext>. The media folder layout flag indicates whether the additional /Music folder will be present inside the media folder. If Album Artist is not blank it will be used for Artist in this layout. Enabling the option will check and if necessary rearrange content to match this layout. CD rips, format conversions, and store downloads always use the standard layout.

Copy files... when enabled ensures that newly added media is always copied into the media folder if added from some other location. You can use File > Library > Organize Library > Consolidate Files to copy anything currently known to the library that isn't inside the media folder. Enabling the option doesn't automatically copy anything. You may get a prompt to consolidate when changing the designated media folder.

tt2