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Yebubbleman

macrumors 603
Original poster
May 20, 2010
6,049
2,636
Los Angeles, CA
For a variety of reasons, I'm sort of tired of having to manually keep my iTunes library in sync across multiple computers. I'm also tired of having only one single computer be able to sync my iTunes library to my iOS devices at a time.

To remedy this, I'm looking into stashing my iTunes library on a cloud-based file service (i.e. Dropbox, OneDrive, iCloud Drive, etc.). Does anyone have any insight or experience with doing this sort of set-up?
 
There are ways to easily synch iTunes media between Mac systems via file system synchronization, Carbon Copy Cloner being one. It is sort of a waste of disk space and a little inconvenient, although all you have to do is fire up the copy task(s) when you make changes to your library.

Plex has a Cloud feature which will allow you to access content from Box, Dropbox and Google Drive:

https://support.plex.tv/hc/en-us/articles/201889756-Cloud-Sync-Overview
https://support.plex.tv/hc/en-us/articles/203082447

However there are severe limitations, such as the media is optimized [likely degraded], and it is not fit for large libraries.

Your best bet is to setup a Plex server either on a Mac or a NAS. There are other servers out there but I'm most familiar with Plex. You could do your NAS library maintenance on your Mac (I pointed my iTunes to a Music folder copy on my NAS which seemed to work, but maybe someone with more experience can comment). You would then set up a Plex server, which could either be on your Mac or your NAS and point it to the iTunes content. I purchased a NAS that has a Plex server so I don't have to keep my Mac running, both for power and security reasons. I copy my Music folder to the NAS via Carbon Copy Cloner so it also serves as a backup copy of my Music library. Or you could put Plex on one of your Macs and just keep that running.

Plex has iPhone and iPad clients which can even access your library remotely, if you want to take the risk of opening a port in you firewall. It can be done relatively safely, but it does require some work. Plex also has the advantage that it supports codecs that iTunes does not, such as Blu-Ray movies that you have ripped to MKV. There are additional programs such as PlexPy that give you data summary options not available in Plex itself.
 
I have not attempted this with a cloud folder, but have done this successfully with local folders.

I don't see why that would not work using a cloud folder. The key is, the entire iTunes directory would need to be in the cloud folder, the .itl and .xml files as well as .itdb are the keys to identifying the contents of the media library, and enable iOS devices to sync to any Mac (or PC) that the device connects to.

But, a few considerations before going down this path. First, do all computers (and your cloud service) have enough space to store the full media library? The cloud services will replicate the files to all of your computers, and store a copy in the cloud.

And second, is the media library organized. I have all of my music on my default /Users/username/Music/iTunes location, but Movies are on a separate USB drive (I have 1.5TB of movies ripped from DVDs). The iTunes database contains links to media file locations in the form of a path. So, that path would need to be consistent on all computers for this to work. In my case, the /Volumes/USBDriveName/Movies would need to be consistent on all of my computers. Further, this alternate Movie location would also need to replicate across computers via the cloud service, else attempting to play content that is not accessible on the other computer would return the dreaded media not found error.

Assuming you library is consolidated in the default location and all media is contained in the iTunes folder, just move the entire iTunes folder to the new location. Do this with iTunes not running on any of your computers. Once sync completes replicating the entire contents to all of your computers, then you are ready to set iTunes to use the cloud folder.

A good way to do this is to launch iTunes while holding the Option (Mac), or Shift (PC) key. This informs iTunes to prompt you to create or select an iTunes library you want to open. Simply select the iTunes library in your Cloud path, and you should be good to go. Any updates on one computer should replicate to all, but I suspect you would need to get in the habit of shutting down iTunes when not in use so that file replication won't run into conflicts with open files on the other computers.

To be safe, you might want to test this by creating a new iTunes Library in a cloud folder and place just a few songs in it. Start by using the Option or Shift when opening iTunes on one of your computers, choose the Create Library option when prompted, and select a cloud folder, add a few songs, synch an iOS device to the new library, then close iTunes. Then, on another computer, use the option\shift method to choose the new library in the cloud folder. If you see the songs you created in the new library, and can sync your iOS device to it, then you know this will work for the entire library.
 
If you use a service like Dropbox, you can selectively sync specific media folders.

That said, iTunes has never played very consistently with remote storage, be it a NAS or a remotely mounted cloud drive. That’s not to say it won’t work, but don’t be surprised if something breaks.

I’d be most concerned about concurrent access, for example.

What I’ve done was stash all of my music in both Dropbox and Amazon Prime Music. I also use iTunes Cloud Library although I find the music matching functionality simply horrid.
 
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