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Keeping Windows & Mac versions of iTunes in sync

May 17, 2008 1:41AM PDT

I have iTunes on a Windows XP desktop computer and another copy on a MacBookPro that I use for music when I travel, etc. I download from the iTunes store and rip CDs that I buy on both machines, which means that one library frequently has songs not in the other. I would rather not continue to copy files manually from one computer to the other - it's hard to keep both computers up-to-date that way. Is there any good freeware or inexpensive software available to keep both music libraries in sync with each other?

I know about TuneRanger, which does what I need, but it costs more than I'd like to spend.


Discussion is locked

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Since both the Mac and Windows versions of iTunes use the
May 17, 2008 3:57AM PDT
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PS. Yes.
May 17, 2008 3:57AM PDT

I did read your post. To sync these you may have to pony up the dough.

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I wouldn't recommend it.
May 17, 2008 11:42PM PDT

Tuneranger is the only game out there, but it has plenty of issues. I just could not get it working reliably enough to trust it implicitly as I can say Synctoy or Chronosync for file syncing.

Having iPhone and Touch, I'm locked out of using better sync / media management software than iTunes under Windows - so after struggling here and there, I gave up trying to keep Win/Mac iTunes in sync, jacked in my Windows iTunes library and dedicated one of my Pros to iTunes syncing duty. This Pro is the only OS X machine attached to my main shared music library.

I did also have to give up trying to sync playcounts between computers but it hasn't been a big deal - I only really need to keep tabs on that for portable use, which means for me it's not a big deal having the info sitting only on the Pro which is dedicated to syncing with the iPod.

This doesn't mean I can only have music on the Mac - it just means I can only change the contents of the iTunes library (and therefore the shared music library) on that particular Pro. The actual folder that the iTunes Library music is stored in on a Windows server.

Then on the Windows machines I use j.River Media Center (the budget minded can use Mediamonkey Gold for $20, half the cost of j.River) which hooks into the shared library and has the capability (unlike iTunes) to automatically monitor changes to the library. So all changes made by the Pro in iTunes to the shared music folder, Windows machines can automatically monitor and register changes.

Having iTunes installed in each of the Windows machines you want to use to listen to purchased tracks and having each machine registered to iTunes will mean that Mediamonkey and j.River Media Center will be able to play back secured iTunes Store purchases.

You'll notice that the above (auto-monitor of music library additions) is only possible on Windows machines, so you really have to manage your iTunes library on the Mac side however you try and do this. Since your Mac is a portable, this complicates things since your music needs to reside on the Mac itself... and you'll need to bring in Chronosync or similar into the equation to sync Macbook-stored music library to the Windows machine.

A monumental pain, no?

Basically the lesson of this is that iTunes+iPod is great for making music a no-brainer experience if you only have one computer. It makes it a nightmare if your needs go beyond that.

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Bad dreams.
May 17, 2008 11:49PM PDT

In a new post I'd like your thoughts on SYNCBACK. But my subject title "Bad dreams" is more about the nightmarish sync issues here. Let me share I have no real sync issues since I'm in the stone age with MP3 titles in a simple old directory system unscathed by iTunes or other organizers. Yes I own an iPod and use iTunes. Gotta spend time with FLOOLA some day.

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So diatribes aside, how to set that up...
May 18, 2008 12:19AM PDT
1. First, share your music folder.
On the Mac (if syncing from WINDOWS): Identify your iTunes music folder. Share it.
On the PC (if syncing from OS X): Identify your iTunes music folder. Share it.
I'm assuming you know how to get Windows and Macs to talk to each other via SMB.

2. Purchase Windows software.
Either Mediamonkey Gold (the paid-for edition of Mediamonkey which adds automatic folder monitoring) or j.River Media Center. There are other freeware which will also allow you to do this but their setup is much more involved.

3. Setup Windows software to look at the iTunes music folder on the Windows machine.
So if you had your Windows iTunes music folder in c:\documents and settings\user\music\itunes\itunes music, point Mediamoney or j.River there as the default library location. Enable the automatic updates lookup on that folder as well in either application. Now, either app, as long as it is running will automatically reflect any changes made to your iTunes music folder.

3 and a bit. Install iTunes on Windows machines and register them under iTunes to be able to play back iTunes Purchased tracks.
You'll need to do this otherwise Mediamonkey and j.River won't be able to play back iTunes Store music. You don't need to import any music into iTunes in Windows since you'll be using MM/JRMC for playback.

4. Set up the sync.
If you do it FROM Windows, you can do it for $0. If you do it FROM OS X, it will cost you $30 for Chronosync - which is a handy app to have around in any case. However Microsoft's Synctoy - an equally useful tool - is free for Windows.

The practical upshot is actually the same, but if your Mac is mobile you might like to do the sync FROM OS X using Chronosync so that you don't have to enable file sharing on the Mac and be able to lock down your firewall tighter.

If you're syncing FROM Windows, you need to connect to the shared iTunes music folder on the Mac and set up a sync in Synctoy between the Windows iTunes music folder and the shared folder on the Mac.

If you're syncing FROM OS X, you need to connect to the shared iTunes music folder on Windows and set up a sync in Chronosync between the Mac's iTunes music folder and the shared Windows folder.


So what will happen once you have this all set up is that once you hit sync in Chronosync or Synctoy, it will synchronise the music files between your Mac and PC. The software you'll be using on the Windows side, be it MM Gold or JRMC, will be able to detect any changes to the library and you'll be able to see and play back all the synchronised files.

The one thing you can't do under this setup is to make any changes to your music from Windows - because although you'll be able to sync those file changes over, iTunes on the Mac won't see them without a cumbersome re-import. All the changes to your library will have to come from the Mac. Podcasts, track renames, deletions, etc - will have to happen on the Crudbook.
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This may help
Dec 9, 2009 9:27PM PST

Don't know whether this helps, but there's a freeware called SyncMate ( Has a lot of syncing options, you can try.