Building a central multi-user iTunes server that works consistently and well— that's also easy to configure and maintain without needing remote administration tools or command line hackery—is annoyingly difficult. However, if you've got a whole mess of ratings and other metadata you'd like to preserve, keep reading.
To start, make sure the network share you want to use is mounted, and that you've got the correct permissions on it. Almost immediately, the copy job failed with a cryptic, absolutely unhelpful error message that said, simply, "Copying files failed. Because of the scattered state of my aged library, I had to then spend about another hour going through the library, re-linking missing files.
One final thing needs be done: with your library on a network share, it's important for that share to be mounted before iTunes starts up. Folks with small iTunes libraries won't see much benefit from this, but if you've got a tremendous amount of stuff in your iTunes library along with some external space to store it, this is an excellent way to give you back a whole bunch of space on your boot volume. This method works well with local disks, too, so if you have a big USB or Firewire external drive and you want to put your media on that, simply setting it as the library location in iTunes should do the trick—you won't even have to deal with the file system issues I had, since a locally attached external disk will almost certainly be formatted with the same filesystem as your source volume. It's never a bad idea to have a full, local backup of important data you wouldn't want lost. There are a few ways to back up your iTunes library and your music to put your mind at ease. If you have Apple's Time Machine backup system enabled—or any other cloud- or system-based backup—your iTunes library should be automatically backed up by default.
If you're not employing a Mac-wide backup service (really, you should get on that), or you just want to back up your iTunes library, specifically, here's how to go about that. If you don't have a backup and your songs are scattered across multiple computers, you can use iCloud Music Library with an iTunes Match account to unify your libraries on one computer. The cloud icon shows you whether those songs are downloaded locally to your device or not; if not, you'll see a cloud with a downward arrow. I've created a couple Smart Playlists that work well for this, as well as for mass-downloading of all my music to my iOS devices.
I like that I can select to 'Make Available Offline' for this playlist on my iOS devices as an easy way to bypass the iTunes Match download-as-needed functionality. The only purpose for this playlist is just a way to quickly confirm all my music is checked -- occasionally a misclick here or there and a track becomes unchecked -- this playlist lets me quickly confirm and fix it. Here's what I did: I opened the view in iTunes where I could see all my songs as one long list.


For starters it will give the user an exact duplicate of their iTunes library in the same location as the old one which will almost certainly cause confusion both in iTunes itself, and to the end user. Sometimes slow, sometimes crashy, and perpetually gaining features, it's the app we use every day but rarely with any joy.
It's not the house iTunes server we wish we had, but it does get your data off of your computer's local hard disk drive. We're not going to describe how to get your music centrally situated and available as an attached library for all your iTunes clients. We're focusing only on taking your iTunes library and relocating it out of your home directory and onto a NAS (though the instructions will work mostly the same with a direct-attached external drive). When enabled, iTunes takes care of the file names and folder structure of your media library. You can follow along with an external drive, though not all of the steps will be applicable. The answer is that you totally can, but you'll lose metadata—play counts, ratings, last-played dates, and everything else that iTunes keeps in its database won't survive a manual copy. Create a target directory inside the share, so that you have a specific folder to point iTunes at. This bumped right into the 255-character filename limit on the Synology's ext3 file system, and the entire copy job aborted.
The first thing iTunes did before even starting the copy was update its internal library so that all its contents' locations were set to the new Library location, so as far as iTunes was concerned, everything was already copied. This wouldn't have happened if the initial copy hadn't failed, which wouldn't have happened if I'd not had that one tremendously long file name. The actual iTunes library file with its metadata is still on my local HDD, but all of my songs, iOS apps, and audiobooks are safely on my NAS. Stay tuned, though: we'll look at some methods for achieving a full-on iTunes server in the near future.
My music—at least for me—is one of those must-backup items; I don't want to have to manually re-build or re-buy thousands of tracks. This way, if you ever need to restore, you can just pop back in Time Machine's History (or a past backup from CrashPlan or Carbon Copy Cloner, for example) to retrieve it.
You can download that track by clicking on the cloud icon, or by selecting multiple songs and control-clicking on them, then selecting Make Available Offline. The "For You" tab makes me wonder why I have a library at all since it seems to offer me multiple playlists and full albums each and every day which all cater to my personal preferences.


One of its more frustrating aspects is its lack of an officially supported server component—Apple seems stubbornly unwilling to provide a real iTunes server, and so folks who would otherwise happily centrally locate a media library on a perfectly suitable NAS are stuck with islands of music.
This is an anathema to some folks, especially music collectors with their music carefully organized into expertly curated deep folder structures, but it's a requirement for this process.
Worse, the location of all my iTunes music had been altered in the library, so a quick perusal of iTunes showed that every single item in my library was now listed as missing. Fortunately, the automatic library organization actually worked for me here, handling the deletion of extraneous folders after I'd fixed the song names. My poor library has been with me since, surviving version upgrades from 4.1 to 11, even going through a platform switch from Windows to OS X near the end of 2007 when I converted. If you start iTunes without having its NAS share mounted, it will freak out and say all of your library files are missing. New files dragged-and-dropped into the library or new iOS apps downloaded from the app store are all automatically stored on the NAS in the library location. That gave me an isolated copy of every song in my library which I can do anything I want with. Still, that's 50GB of SSD space that would be taken up by files which, frankly, don't particularly benefit from being on an SSD. The movement of the library is an automated thing, and it relies on iTunes being able to automatically place the files where they need to be placed.
You'll get a file picker dialog box, which you should point at the network folder you've previously created.
As iTunes has gained features, it's directory layout had changed, and as a result I've got crufty extra directories and files stored all willy-nilly behind the scenes. There is plenty to discover in "For You", and I can call up any song or album I want to hear in the search, even queueing up the next song while listening to the current one.
I could relocate them to an external drive, but I don't have any spare external drives with enough capacity. Even third-party tools which automate some of the annoyances are at the mercy of iTunes updates breaking everything.
If I have an absolute catastrophic failure on my computer, I can just get up and running again and then just drag all my songs back into iTunes and all I lose are playlists which I can rebuild.



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