Moving iTunes to External Drive NOT Working?

So here I've downloaded an episode of a TV show, copied the file to a different drive, deleted the original and emptied the trash. All to ensure that iTunes cannot locate the file. When I use Get Info iTunes tells me that it used to be at:

file:///Users/steve/Music/iTunes/iTunes Media/TV Shows/Black Books/Season 1/01 Episode 1.m4v

I know where I moved it to. I can copy the path and filename separately from Finder's version of Get Info. It's here:

/Volumes/Big Data Drive/iTunes/iTunes Media/TV Shows/Black Books/01 Episode 1.m4v

Not only is the first part of the path different, but I didn't bother making a season no. folder on the external drive.

I can make iTunes find the episode again by copying the individual file from the Black Books folder on my external drive to the Season 1 folder inside /Users/steve/Music/iTunes/iTunes Media/TV Shows/Black Books/. I'm hoping I can see a pattern for your library where it might be possible to move or copy a single folder rather than having to make lots of individual repairs, but so far I think I'm only seeing the iTunes half of the picture, not what it is really going on in Finder. 😕

tt2

I find the trick to changing libraries is to click the icon that launches iTunes and immediately press and hold down the option key (Mac) or shift (Windows) and keep holding until you get an option to choose or create a library. If iTunes opens without giving that prompt close it and try again. Click the choose option then browse to the folder/.itl file that you want to open.

After switching libraries make sure the media folder is listed correctly. It doesn't always switch, particularly if the original copy wasn't in a portable shape. See Make a split library portable for details.

tt2

E.g. NOT iTunes. Macs are generally more forgiving when files and folders are renamed, but iTunes should follow the path within the new copy of the media folder on the external drive. This assumes that all content was inside the iTunes Media folder the iTunes folder that you copied across. That said you mentioned copying the entire Music folder. Anything inside Music, but not inside Music/iTunes/iTunes Media is going to remain connected to the internal copy rather than the external one. Consolidating the library to the new media folder should resolve this. As before details in Make a split library portable. Once everything is in the right place you should clone to another drive for security then clean up the excess copies of things.

tt2

See Backup your iTunes for Windows library with SyncToy. Although written for Windows it mentions Mac alternatives for the same task. Basically you should never trust your data to a single hard drive, and ideally you want a backup method that doesn't require you to delete and replace what has already been backed up, or work out what is new or updated and copy that by hand.

tt2

I'm not that familiar with Time Machine, but it might not automatically include the new external drive. You can use Settings > Time Machine > Options to review any exclusions.

The user tip Make a split library portable should have all the background you need to ensure that the active library is on your external drive, and in a portable shape. E.g. your active iTunes Library.itl file library is in a folder called iTunes on the external drive, with the media folder set to iTunes/iTunes Media inside it, and all media consolidated to that path.

tt2

Interestingly, there are only 3 artists in this second Music folder...and they are the ones that have been successfully transferred to the external hard drive when I have changed the location of my library.

I had a whole set of steps typed out before I reread this and realized that as far as iTunes is concerned the bulk of your library is still on the internal drive. Please confirm and assuming that is the case take the following approach (otherwise let me know where I've gone wrong):

1. Create a new folder called iTunes at the root of the external drive, and make a folder inside it called iTunes Media.
   
2. With iTunes closed move the following items from /Music/iTunes/ to /iTunes/ :
   Album Artwork
   iTunes Library Extras.itdb
   iTunes Library Genius.itdb
   iTunes Library.itl
3. Option-start iTunes and open the library file at /iTunes/iTunes Library.itl.
   
4. Under Edit > Preferences > Advanced change the media folder to /iTunes/iTunes Media/ - do not consolidate if prompted.
5. Select the tracks for the three artists shown in the right hand column of your image above, either all at once or in batches, and use File > Library > Consolidate Files to copy these into the new media folder.
6. If I understand correctly everything inside /Music/iTunes/ is now content that you manually copied over from the internal drive, but which isn't actually connected to the library. Instead the library is still looking at the copies on the internal drive. If so delete the iTunes folder from inside /Music/ and empty the trash. These should free up the space required for step 7.
7. Now use File > Library > Organize Library > Consolidate Files to copy in all of the media from the internal drive and update the references in the library properly.
   
8. Test the library, allow Time Machine to back it up, delete the old copies of the iTunes content from the internal drive.

tt2

1. When apps are updated the new version should replace the old, and the overall folder size will generally remain the same. In practice iTunes doesn't always discard the older version. Your 58Gb of apps will be all that are currently connected to the library. The version with 115Gb indicates that you've either had some failures in this respect, or that you've deleted some unwanted apps from the library without deleting the related files. Only the content connected to the library gets consolidated. In addition the old location for the apps folder was inside the library folder, the newer location is inside the media folder. Restructuring the library at some point may have left unwanted duplicates.
   For apps you can unhide any hidden past purchases and use Music > iTunes Store > Quick Links > Purchases > Apps > Not on this Computer to locate downloads of any apps that might be missing from your collection.
   
2. On a Mac Books are no longer stored in the iTunes Media folder but go to some hidden cloud connected cache in your profile's library folder. The Downloads folder should be created as needed, and should be empty or removed when not actively downloading any content. The iTunesU folder should hold any iTunesU content. Have you downloaded any?
   
3. Again consolidation only pulls over content that was connected to the library. If you think there are files that are on the internal drive that should be in your library, but aren't in the new version of it, then copy these into <External>/iTunes/iTunes Media/Automatically Add to iTunes to add them to the library. Otherwise you could be looking at items that you deleted in the past, but didn't send to the trash. Newly imported video files are generally treated as Home Videos, audio files as Music. You may need to adjust the media kind after import.
   
4. Yes, you can let the old Previous iTunes Libraries folder and .zip go.

The discrepancy in folder sizes is quite big. You'll need to explore things carefully to see if you can make sense of it, but it sounds like at least part of it will be down to the two different copies of the Mobile Applications folder.

tt2

I'm expecting to see some discontinuity between the two paths. E.g. something like this:

• file://localhost/Users/username/Music/iTunes/iTunes Music/TV Shows/Friday Night Lights/Season 5/101 Pre-Game_ The Cast Looks Back (HD) 3.m4v

• Users/username/Music/iTunes/TV Shows/Friday Night Lights/Season 5/101 Pre-Game_ The Cast Looks Back (HD) 3.m4v

So in the case the mismatch would be the additional iTunes Music folder.

Also, there are hundreds of Podcasts that are in iTunes when I open it, but not listed as files under Podcasts. Are those stored somewhere else?

What appears to have happened is that some of the content listed in your library wasn't where it was expected to be. Because it wasn't there it hasn't been consolidated. If it can be moved to the expected path then you can restart iTunes so that it tries to look for missing content in the expected places again, then consolidate once more.

The alternative approach is to move the files to the correct position in your new folder structure, then attempt to repair one of them. iTunes should be able to find the rest.

If nothing else works you can delete the broken entries and add in the missing media via the Automatically Add to iTunes folder. But I'd start with option 1.

tt2

Select one of the problem files, press Cmd+I to Get Info, say no when asked to locate the file, then look on the summary tab for where iTunes "thinks" the file should be. The path will begin file://localhost/. Where is it really?

I'm expecting something like this:

• file://localhost/Users/username/Music/iTunes/iTunes Music/TV Shows/Friday Night Lights/Season 5/101 Pre-Game_ The Cast Looks Back (HD) 3.m4v
• Users/username/Music/iTunes/TV Shows/Friday Night Lights/Season 5/101 Pre-Game_ The Cast Looks Back (HD) 3.m4v

You don't need to add the highlighting, but I need to be able to see what is different between the two paths. If you copy and paste one path to help you make the other make sure you update it to show the correct details.

tt2

Yep, I'd initially misunderstood what you meant by this bit.

Not sure if anything was supposed to happen on the screen to signify the change, but nothing did.

Try closing iTunes, rename the iTunes folder on the internal drive, then open iTunes again. See if tracks are being picked up on the external now.

tt2