Keeping iTunes library in sync across two computers

So, I’ve been researching this topic for a while now with no satisfactory solutions, so I figured I’d ask here…

Does anyone have a good solution for keeping an iTunes library in sync acros two computers - my laptop and desktop - that doesn’t involve Apple Music’s syncing service (which by all reports is still a bit of disaster.)

I’ve got a collection of about 30,000 tracks, mostly from my own CDs but some from online purchases and a number from out of print LP records I own. Given the number of stories I’ve heard of people’s collections disappearing when they activate Apple Music Match or whatever they call it now, I really want to avoid that, (and I’m not really interested in another monthly fee anyway.)

When the old iTunes OSX app was current, I had pretty good success keeping the media folder in Dropbox and accessing it from both computers, as long as I didn’t open both apps at the same time. (Yeah, I know this was a little risky but it worked for years without incident.) When OSX went to the Music app, this option no longer seems to work reliably.

I know I can host it on a local server and access it from multiple devices, but I’d like to have the library available on my laptop when away from home.

So any other thoughts on this? Much appreciation in advance for any help.


I wonder if you could use something like Syncthing to keep one Mac’s ~/Music/iTunes folder basically synced up to another Mac’s. I’ve never done this myself, but I know that iTunes can be pointed to using a specific folder as its media library. I would think that means you could make a copy of another Mac’s iTuens Library and direct your iTunes to use that. If you use a tool like Syncthing to keep both directories sync’ed I would assume that should work.


I use Apple Music and iTunes Match. Not a disaster for the most part, I have everything well managed these days. (But I have only about 6600 items.) I know at first iTunes Match was limited to 25,000 tracks, but I believe the limit is now 100,000 tracks.

I’d be very, very careful to make sure that only one computer is accessing a Music/iTunes library at any time before doing something like this. It could get ugly if two computers are trying to update the library in different ways before syncthing can manage this.

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That’s certainly an excellent point, @ddmiller. I realize I had been tacitly assuming these would not be used concurrently but rather one Mac at a time.

Indeed, if you want to use both instances of iTunes simultaneously, I would expect issues to arise with any local syncing operation and in such a case I would wager you’re essentially almost forced to go the Apple Music syncing route instead.

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Just my solution, will not work for everyone.

I run a very large Plex server, runs on a Raspberry Pi 4b with several large SSD’s attached.
Then throw my “iTunes” or Music library at it. Along with all my movies. Access anywhere, on any platform. Works great.
Note: Plex has gotten better with music in the last year or so.
Now has a dedicated music app for IOS.


When it works, this is great. But I’ve read too many anecdotes describing disasters when it doesn’t work. So it’s not a solution I recommend.

Do you actually need the files on two computers at once?

macOS supports media sharing. One Mac (with the library) can make it available for streaming to other computers running iTunes/Music on your LAN. And if you also enable Home Sharing, then other devices (like my Apple TV and iPads) can also stream them if they are logged in to your Apple ID.

I also sync my music to an iPod Touch, which is my preferred music player when I’m on the go. It also has no problem playing to HomePods.

Getting away from iTunes/ altogether is worth considering, so Plex is something to at least think about. iTunes was crap but is worse crap, so unless you have compelling reasons to stick with Apple’s products (which I do, unfortunately), you might find that Plex could meet your needs as a music media server.

Keep in mind that tracks purchased from iTunes Store probably won’t play on Plex, just as movies purchased there won’t, due to copy protection.


It might be better if I contact you directly but I’m looking at something similar (running Plex on a Synology NAS).

Does such a solution mean abandoning iTunes and moving to “Plexamp” or something similar?

Looking for a solution that will run under Windows 10, MacOS, iOS 15.5 and on an iPad as well as accessing AirPlay, etc.



Yes and No. It depends.

I have no experience running Plex on Synology, but I have seen tutorials and it seems to work.

The Plex client runs on anything anywhere. So you can play music with that. No you do not have to give up on iTunes/Music. but there are some limitations. Best if you set only one machine and only one Apple music account to sync to the Plex server. Music downloaded from Apple music service, will not play. If you buy the music at the Apple music store, you will have to “fix” it to play on Plex.

I have and use an Apple Music subscription, but only for discovery. I buy all my music elsewhere. Bandcamp, or Resonate, or direct from artist. Then add the to my iTunes/Music, on the one machine the syncs to Plex.

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In the old days, before I signed up for Apple Music, I used to use SuperSync: It worked reasonably well. I’m not sure if it’s still a good solution, given the change from iTunes to

Hey, thanks everyone for the plethora of ideas and feedback. Much to digest here. I’m intrigued by Plex and will explore, though it’s not clear how convenient it would be away fro home, but I’ll delve into it.

I pretty much do need access from multiple computers. In part for travel and in part because I’m a musician and also use a program called Transcribe that lets you slow down audio file and put all sorts of bookmarks and cue points in an audio file. Transcribe creates it’s own data file that’s quite small and just points to the original audio file without modifying it. It’s great for studying recordings and solos and learning tunes. So I keep the Transcribe files in a separate folder, but they point to various files in my iTunes/Music media folder.

Thus having copies on both the desktop Mini at home and my laptop when traveling is very helpful.

I have felt tied to Music since I also still use my iPhone for listening to tracks when in the car, but I’m seriously considering moving mobile listening to a mp3/third party “iPod” option. There are some high end options that look intriguing, if pricy.

So I’ll delve into all the ideas here and see what might work. If anyone has more thoughts, keep 'em coming. I’m wide open still.



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If your tracks are streamed (e.g. Apple Music subscription), then you’re stuck with Music.

Similarly, if you have FairPlay DRM-protected songs (early iTunes Music Store purchases), they force you to stay within the Apple ecosystem. But they can be sync’ed to off-line devices like iPods.

But with DRM-protected songs, you have the CD burning loophole here - you can burn these tracks to an audio CD and then rip them back. The results will not be DRM protected, but there will be some generational loss in audio quality from the re-compression (unless you rip into an uncompressed or lossless format).

For tracks that are stored locally and are not DRM protected, you have lots of options.

You can convert files to different formats (e.g. from AAC to MP3 or vice-versa) from within Music:

  1. Preferences → Files → Import Settings…

  2. Set the format you want and click OK. I typically use AAC at 128 Kbps, VBR (a custom setting). You may prefer an MP3 format for maximum compatibility with third-party tools.

  3. Select the songs you want to convert

  4. File → Convert → Create AAC Version (this might be Create MP3 version, or some other text, depending on the format you selected in step 2.

  5. When the conversion completes, you will have two copies of each track in your library - the original and the converted one. You can then copy the converted file out of the library (see below) and delete it to avoid wasting space in your library.

To export files from Music/iTunes, just drag the tracks from Music to a folder on your desktop. The underlying files will be copied to that folder.

Once you have copied the files out of Music, you can do anything you like with them, including:

  • Edit/convert with your favorite tools (e.g. the open source Audacity)

  • Import into a third-party music player app

  • Sync to a non-Apple music player device

  • Copy to a USB flash drive for playback by other devices.

    Many car stereos will read a USB drive and play music files from it. See your owner’s manual for the file formats supported and the way it expects the drive to be formatted.

    Similarly, many consumer appliances (TVs, home theater amplifiers, etc.) have a USB port and they will play music files stored on a connected device. Again, see your owner’s manual for the file formats supported and the way it expects the drive to be formatted.

Once upon a time, I used these techniques to burn MP3 CDs - data discs with directories full of MP3 files. I would bring them on trips for playback in my car (its CD player supported MP3 discs), so I could bring hundreds of songs on each disc.

Unfortunately, car stereos with CD players are not common anymore. But USB ports that can play a thumb drive full of MP3 files are common, so that’s the modern equivalent.

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As a somewhat educated guess what I might try doing if you wish to keep your entire music library synced between the 2 machines is to have a 3rd machine that is always on with your music library in the Shared folder to avoid permissions issues. Then keep your music library on each of the machines in its normal location. Then you should be able to use one of the many free sync apps available (many are free if you only try to sync 2 files or folders) to sync the libraries with the ‘server’ library by mounting the ‘server library’ and running the sync app at that time. It would require you to do this manually on occasion but it would do the job. Given I do not do frequent changes to my library this might work for me.

If you do not have another computer, you might have the ‘server library’ on one of them as well as the '‘local library’ and use the ‘local library’ with Music. Another way would be to move a copy of your music library to iCloud, OneDrive, or Google Drive. Then using their respective Apps to sync each machine to the music library on the cloud server. What you would have to remember is to do the sync with the machine right after you made any changes to your ‘local library’ so that the cloud library would have the latest changes on it when synced to the other machine. However, depending on the size of your music library, this could cost some money for extra storage space. Another downside of this is that you need to have an internet connection when syncing.

What also might work is to store your local music library in the cloud servers App folder on your machines. This would place the most recent copy of the music library on the cloud server as well. The issue with this, aside from needing to have an internet connection for updating, is that if you used Music on both machines at the same time, it might lead to corruption of the music library. The advantage of this is that the entire process would be done without user intervention and you would have the latest synced version of your library available without an internet connection as well as a constant backup of your music library on a cloud server.

Please understand that this is all theory as I have not attempted any of this myself. I strongly urge you to make a complete backup of your current music library before trying any of this as I am not sure it would actually work.

What I am currently doing is having my music library and my downloaded or copied music on an external drive and making an alias of the folder containing it in the music folder on my boot drive. The folder on the external drive is named the same and in the same configuration as the would be default folder on my boot drive. Time Machine also backs up the external drive. This way I can use a smaller less expensive boot drive and should I have boot drive corruption, if it should fail, or need to do a reinstall my music library is left safe and intact and all I need to do to get things working again is to recreate the alias and adjust Preferences in the Music App.

I’ve been trying different methods to do this for several years now. I have two macs with 2 main users, so multi-computer and multi-user on each computer. About 2500 albums/26000 tracks. I tried networked libraries, but iTunes/Music doesn’t like them. Things slowly start to go haywire, lost music files, artwork, random stuff goes wrong. I tried Supersync, but I could never get it to work correctly. Not sure how up to date it is either.

I don’t like how the built-in library sharing works, so I don’t use that. I never tried iTunes match since i heard many bad things about it for people with large libraries like myself.

I tried using regular sync software to automatically keep the libraries in sync, but since Music doesn’t automatically pick up new files you have to manually add them so it’s not much of a savings. And if you change the tags on one mac, the new files get copied over but Music won’t pick up the changes so it’s not a full sync.

I finally just gave up and each computer has a copy of the library. I try my best to keep them in sync. Each time I add music on one computer, I also add it to the other. On each mac I designate one user as the main and add all the music files through that user, and their prefs in Music are set to copy to the library and to keep the library organized. The other user(s) are set to not copy to library and not organize. The secondary user(s) you add music that is already put in the library area by the main user. You need to make sure all the users can read the music files, so you need to do some permissions fixing in the main user’s Music library folders, or wherever you store it. On one mac I have it in the Shared user folder since the main drive is large enough, on the other it’s on an external USB drive. The external USB drive means you don’t have permissions issues between users, but iTunes/Music doesn’t like its library getting unmounted which happens when the mac sleeps, so I have to use Jettison to deal with that.

One annoying issue with the multi-mac/multi-user setup if you have multiple Airplay speakers (i have 6) is that often one person will be playing music from one device (a mac, or directly from a phone, etc) and someone else needs to turn it off, and they have to try to figure out which device is playing the music.

I also got so frustrated with the new Music sync interface to my iPhone that I purchased iMazing to do it. I mean c’mon, can’t they even have the app remember a sorting method in the UI?

Given all the issues over time, I have just recently decided to start using Roon as my primary player. It has a different method - you designate one master library server and everything else is just a remote, but all of them show the same way so it’s not apparent. This also means it’s easier to deal with multi-users and multi-Airplay speakers. But it is subscription. It can broadcast to Airplay, sonos, google-cast, and has its own hi-fi transport method (RAAT) that works with certified equipment, most of which is expensive. If you’re not in it for hi-fi experience, it is probably overkill. But it certainly makes the multi-mac/multi-user situation waaaaay easier to deal with.

Not thought this through, but I would look into having a slave/master solution using the «Automatically add to music» folder on your laptop.

I have used this for many years manually from my Mac Pro 2009, with the «Automatically add to music» folder via SMB on a Mac mini. It has been very reliable.

If you only need to access iTunes (Apple Music app) from one client Mac at a time, you can share the music library among multiple client Macs by moving both the Media folder and the music library database file to a shared volume and configuring iTunes/Music on each client Mac to use the shared database file instead of its own database file.

  1. On each client Mac, launch Music/iTunes, go to Prefs > Files, and UN-check both “Keep Music Media Folder Organized” and “Copy files to Music Media folder when adding to library”.

  2. Quit Music/iTunes.

  3. Go to the Music folder in the home folder of each client Mac and rename it.

  4. On the shared volume, create a folder that will contain the music library database and the media folder. For example, name it SharedMusicLibrary.

  5. On each client Mac, make a compressed copy (for backup purposes) of the music library database file, which is named “iTunes Library.itl” in Catalina or earlier or “Music Library.musiclibrary” in Monterey. (I’m not sure about Big Sur.) It should be several MB in size, and it probably resides in “~/Music/iTunes/” or “~/Music/Music/”. (Do not confuse it with the XML file, which is useless.)

  6. From the client Mac whose iTunes library has the playlists and star ratings you want to preserve, move its music library database file to the SharedMusicLibrary folder.

  7. Trash all the music library database files that you made compressed copies of.

  8. Move to the SharedMusicLibrary folder the Media folder that contains all the media files (m4a, mp3, etc). The Media folder is probably “~/Music/iTunes/iTunes Media/” or “~/Music/Music/Media/”.

  9. In the Applications folder of one of the client Macs, select the Music/iTunes app, hold the Option key, and double-click it. It should display a “Choose Library” dialog with 3 buttons. (If you don’t get the 3-button “Choose Library” dialog, repeat this step.)

  10. Click the “Choose Library…” button.

  11. In the resulting open dialog, navigate to your previous music library database file in the SharedMusicLibrary folder, either “iTunes Library.itl” or “Music Library.musiclibrary”.

  12. Music/iTunes then will display a save dialog asking you to create a new Music folder alongside the one you renamed in step 3. That folder should remain empty.

Now all your music tracks and playlists should appear in Music/iTunes.

Weirdly, on my Monterey system, the Music app did not display any window at all at this point. You may have to choose Window > “Bring all to front” or Window > Show Activity to make the window appear.

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You did not say which OS you’re using but older versions of iTunes can still be used by installing them through the Retroactive app:

I still use iTunes 10.7 with CoverFlow with Catalina and it works fine. Running under a VM for Big Sur and Monterey, it also works with those systems but I don’t know if it would be different running under the actual OS. One thing that does not work for iTunes 10.7 using a VM is the CoverFlow art but regular icons are fine like in album view.

Since I have multiple computers using iTunes (all using 10.7), I also want those to have all of the music from my main computer. I tried different things in the past but eventually went with two things: using CCC to clone my music files to the other computers, or if I only rip a few CD’s I just manually copy those to the other computers. When I use the other computers, I can just use the Add To Library command and iTunes can run through the process which is usually under five minutes but a bit longer for my one older PowerPC unit. If I only add a few CD’s, I can just add those manually. All of my files are from my own CD’s or digitized records/tapes so I can’t say how this works with downloaded files. I did try to use the Automatically Add To iTunes folder but something didn’t work as expected although I don’t recall what that was so I use the other methods. I have around 36,000 tracks.

Since you stated you want to take the laptop away from home, using CCC is one of the easiest ways. If you add playlists, you could just export those and copy over to the laptop. One reason I don’t use a shared folder is because that computer would need to run all the time or at least most of the time and I would rather have the files on each computer as backups as well.

If you are tempted to share music among multiple computers using iCloud and Audacity, it can get a bit tricky. I have been digitizing my old music library by recording it on Audacity with a MacBookAir set up next to my component stereo system, storing the Audacity files on iCloud, then editing the iCloud files on my desktop. If I don’t get the Audacity files fully closed and completely compressed on the Air, sometimes they will not open or get munged if I open and try to edit them on the desktop. Closing the Audacity file or even shutting down Audacity on the Air will not always fully update the iCloud version accessed by the laptop.

Thanks again, everyone, for the depth of your responses. It’s given me a lot of different directions to explore.

I’m running Big Sur still and while downgrading Music to an older version may be possible, it seems like a pain and probably not a long term solution. I tend to run a few versions behind the current OS intentionally, but eventually I’ll need to upgrade and keeping legacy software functioning is a challenge.

I’ve installed and paid for month of Plexamp to experiment, and I’m cautiously optimistic it may be part of a solution. I’m not a huge fan of the interface, but I can work with it. It seems to stream well from the server to both the laptop and my phone. My biggest complaint is that while it sees Genre tags, it doesn’t seem to see Grouping tags, which I use to denote subgenres of music, e.g. Bossa Nova, Samba, etc within a larger Brazilian category. But I might be able to work around this with playlists. We’ll see.

I also haven’t tested yet to see if there’s a way for Plexamp to resume playing a file where I stopped previously. I record a couple 2 hour radio shows off the internet each week to listen to later, and it would be nice to be able to “remember playback position” like Music does.

Plex still doesn’t solve that issue of having the music files on my laptop too, for use with Transcribe for music study purposes. But honestly I’m only studying a few dozen pieces at once, so maybe I just keep the active ones in a shared folder that both computers can access. Sometimes one solution just can’t solve all problems.

Anyway, thanks again everyone! Love this community!