iTunes Library organization in one folder...

1. Backup both your library and media folders. What follows should not cause any problems but you should be doing this already and in the unlikely event that something goes wrong and you don't have a backup you will kick yourself.
   
2. Use File > Library > Organize Library... and tick both Rearrange... and Consolidate... boxes. This will ensure that iTunes moves everything into the modern structure. Your mobile applications will either be moved over to the /Volumes/Drobo/iTunes/Mobile Applications folder or be copied, not absolutely certain, but once the process is complete you can delete the Mobile Applications folder on the internal drive.
   
3. With iTunes closed Copy the library files and Album Artwork folder from /User/Music/iTunes to /Volumes/Drobo. If your main iTunes Library file is called iTunes Library and not iTunes Library.itl rename the file you have copied over.
   
4. Hold down alt/option as you launch iTunes. Keep holding until prompted to choose or create a library. Click choose and browse to the iTunes Library.itl file.
   
5. Check that the library behaves properly. If not ask back here for further directions, otherwise close iTunes and move on.
   
6. Rename the folder iTunes as iTunes Media, start iTunes. Check under iTunes Preferences > Advanced that the media folder now reads /Volumes/Drobo/iTunes Media. If not correct it, close iTunes, then reopen. Check that the library behaves properly. If not ask back here for further directions, otherwise close iTunes and move on.
7. Create a new iTunes folder at the root of the drive, i.e. /Volumes/Drobo/iTunes, then move the iTunes library files, Album Artwork and iTunes Media folder inside the new iTunes folder.
8. Hold down alt/option as you launch iTunes. Keep holding until prompted to choose or create a library. Click choose and browse to the iTunes Library.itl file inside the new iTunes folder.
   
9. Check that the library behaves properly.

Assuming all is well update your backup and then remove the redundant iTunes folder on the internal drive.

Should you find that performance suffers copy the library files and album artwork folder back to /User/Music/iTunes and switch libraries. Move the files back to the Drobo and access on that path in preparation for moving to a new computer or drive.

tt2

Hi tt2,

Thanks for that detailed list, all seems to have worked except for a few strange things.

When I clicked on organise and consolidate it seem to add songs/albums into various folders within my old /Drobo/iTunes folder (for example: Music, iTunes Music folders both appear within /Drobo/iTunes)??

Further to that, having completed all steps, /Drobo/iTunes/iTunes Media/ now has within it folders including /Music and /iTunes Music, each with certain amounts of music, and also folders relating to album covers (although not the same size as the one within my new /Drobo/iTunes path).

Finally, when I do listen to any random song, it seems to appear outside of /Drobo/iTunes Media, right into /Drobo/iTunes where the library files are?

Any suggestions?

Check under iTunes Preferences > Advanced that the media folder now reads /Volumes/Drobo/iTunes/iTunes Media. If not correct it, close iTunes and reopen.

Check under File > Library > Organize Library... that the rearrange box is greyed out. If not tick it. Tick Consolidate files. Click OK. This will copy anything that has ended up outside the media folder into it.

Under Edit > Preferences > Advanced turn Keep... off, click OK, then go back and turn it on again. This should enforce the internal structure of the media folder.

You will need to manually tidy up any media files that now lie outside of the media folder. There may be a redundant .xml file at /Volumes/iTunes/iTunes Music Library.xml which you can discard. You might also want to prune some of the older files out of the Previous iTunes Libraries folder.

You should now have /Volumes/Drobo/iTunes containing the library files and the folders Album Artwork, iTunes Media, and Previous iTunes Libraries. /Volumes/Drobo/iTunes/iTunes Media should contain the folders for various media kinds. All artist folders should be down in /Volumes/Drobo/iTunes/iTunes Media/Music.

tt2

tt2,

You are an absolute legend! 😎

I followed your instructions, took me a while to move all music neatly into the /Music folder and make sure all other folders where in the right place, I also I unticked/ticked 'Keep iTunes' after clearing up too.

Anyway, touch wood, all seems to be looking good and songs are playing, updated some apps and they downloaded into the right folder!

I can't praise you enough pal, thanks so much for the instructions and follow up!

Quick question, now this is all done, when I come to do a clean install of Yosemite, when I option click iTunes I select the iTunes Library.itl file and thats it? Will I need to set the pref/advance/location again?

Thanks again. 🙂

You're welcome. 🙂

Option-start-iTunes and choose the .itl on the external drive should be all you need to do.

tt2

You're welcome. 🙂

tt2