iTunes 9.2: Why can’t we sync playlists yet?

It was Wednesday afternoon last week and I was packing to head out on a business trip. This usually involves syncing my iDevices so I have the latest tunes, Apps, movies, etc. that I want to take with me on the road. All of this syncing works great between devices, except when those devices happen to be computers! My main music library is on a shared family iMac in a central part of the house. It has music on it from each family member according to their tastes in music. As you might imagine I really don't want to bring a bunch of music with me that I have no interest in listening too. This isn't a problem on an iPod, because you simply sync only the playlists you want to take with you and only those songs will go onto the device. 

So why does Apple exclude computers from all this syncing "magic"?

I have iTunes 9.2 on my MacBook Pro. I have iTunes 9.2 on my iMac. Both Macs are authorized on the same iTunes account and therefore can legally play the same songs. However, when it comes time for me to get songs from the iMac onto the MacBook Pro it's a very MANUAL process. iTunes 9 introduced Home Sharing. However, Home Sharing is essentially just a network copy feature and nothing more. Although Home Sharing DOES automatically add purchased songs to the other computer, there's no syncing and no duplicate management for playlists or anything else. Grab 10 songs and drag them over and 5 minutes later you can grab the same songs and drag them over again. iTunes will not warn you about any duplicates and it will just copy them AGAIN. This problem got a little worse back when Apple moved to iTunes Plus because although you could "upgrade" your songs and iTunes would replace them with the new DRM free versions at a higher bit rate (keeping your ratings, metadata, play counts, etc.), your other computers would be out of luck for this automatic replacement. You would have to do it all manually.  I guess from time to time you could wipe your library on one computer and copy over again, but the question becomes why is there no automatic way of keeping two iTunes libraries in sync?


Is there a 3rd party solution out there?

I've looked and so far I haven't found the perfect app yet (or even one that's close). Sure there are some Apps out there that will attempt to keep your iTunes libraries in sync. However, from what I've seen so far either the user interfaces are HORRIBLE and overly complicated or they simply don't do enough. For example, I haven't found one yet that syncs "Smart Playlists". Let's say I have a Smart Playlist of my "Best of the Best" songs. They are the ones I've rated 5 stars. So technically it's not a "real playlist", it's a dynamic one that updates automatically based on the song ratings. None of the Apps I've tried to date will handle this. Yet Apple has been able to sync Smart Playlists to the iPod since day one.

Ideally what I want is pretty simple – I want to be able to choose a few playlists on my iMac (including Smart Playlists) and have those SAME playlists sync to my MacBook Pro. If I change the rating of a song on the iMac, then that song's rating should get changed on the MacBook Pro too and therefore it would appear in the proper playlists automatically. If I have manual playlists that I move songs in and out of, this should happen on the MacBook Pro too. 

Yes, I'm very willing to pay for such a solution. Have you guys seen anything out there that really works? It's sad that Apple hasn't built this in directly to iTunes for computers like they have for iDevices. 

21 Replies to “iTunes 9.2: Why can’t we sync playlists yet?”

  1. Boy do I agree, and if there is an app, it has alluded both of us.

    But what about synching your iX with more then one computer. Apple does nto seem to realize that many of us actually own more then one computer. I have an iMac, and a MacBook Pro that I use for traveling. I normally since my iStuff to the the iMac, but when I travel if I try to sync to my MacBookPro I lose everything that is on there, and since I can’t sync either I am up a creek.

    Someone at Apple needs to understand how their equipment is actually being used, and stop this non synching nonsense.

  2. Synching a Playlist is easy and has been in iTunes for as long as i can remember.
    In iTunes go: File/Library/Export Playlist and i save it to the Desktop, or a thumb drive. Then i email it to myself (or transfer with the thumb drive) to the other computer and save it on the desktop. Now in iTunes on the second computer go: File/Library/Import Playlist and navigate to the playlist on your desktop. Double click on it and assuming the music is on the second computer, you’ll see the new playlist in iTunes. As for synching everything else, MobileMe is the only way to go! It keeps all your devices in synch all the time. Well worth the price, can even find your iPhone or iPad should you misplace it. Get it at the Apple Store. Talk nice to them and they’ll usually discount it 30%

    1. Dennis,
      that’s not “syncing”. That’s exporting an XML file (Playlist) and importing it hoping that the same music is on both computers and if it’s NOT then it won’t work. Also what happens now when you update the playlist on one computer? Does the other computer know about it? No! While the ability to import the list of songs is nice, it’s far from a solution to the ongoing management problem and it’s not actually syncing.

      1. Terry,

        Call it what you want, the object is to match up your playlists. It’s easy and requires very little time or effort. To match up all the music on my computers i turn on “Share My Music” in iTunes Preferences. With iTunes running on both computers, select the “Shared” Music Library on one of the computers at at the bottom of the iTunes window select “Show”/”Items not in my library”. Select the ones that you want and click on “Import” to match up the Libraries. Do that on all of your computers and it’s a good way of backing up your Music. Now that all the Libraries are the same when you import the XML file Playlist you can be assured of your Playlists being “in agreement”, which is by definition, “in Sync”.

        1. Hi Dennis:
          Dude, you’re just not getting it.

          In his post, Terry is asking for something iTunes won’t do—-automatically sync. You moment you add a song to one computer, it updates your other computers all automatically. That’s automatic syncing.

          What you’re talking about, is not automatic, and it doesn’t just take a few minutes if you have a lot of songs, and you have to do it over and over again to stay up-to-date.

          Your way is nothing more than a totally manual, clunky workaround. Using your workaround, your computers would be out of sync the moment you import even one song from a CD, or from GarageBand, or anywhere else.

          That’s not automatic, and it’s not what Terry was suggesting was missing. There has got to be a better way to make this all work, and there is—Apple just hasn’t added it yet, which is the entire point of Terry’s post.


          1. Sounds like we need Dropbox for iTunes. It is a pain with multiple Macs and users (parents, kids and college kids). Terry is asking for Dropbox like syncing between computers and devices.

            I agree Apple needs to consider how we work with these.

          2. Hi Scott:
            Didn’t mean to get in a peeing contest with you Dudes, but i think i have got it! By using my totally manual, clunky workaround i have managed to keep my modest 5,000 plus song library and all of my playlists in sync over 5 computers, 3 iPads, an Apple TV and numerous ipods. In fact i can play, pause, stop, start, fast forward, rewind, volume up or down, even turn speakers on or off, all from my iphone using Apple’s free “Remote” App while sitting on my patio sipping margaritas. You have to admit Dude, that’s pretty amazing Software and it only gets better every year. How about that Genius Playlist, or iTunes DJ, just amazing! Instead of ripping it (and me, i was just trying to help with clunky workaround) try forwarding your constructive criticisms to Apple. You never know you may see it in the next upgrade, or you could wait for Microsoft or Adobe to come out with something better,but i wouldn’t hold my breath on that! Oh, and thanks again for autographing your book at the DFW class a few months ago.

  3. Terry. When you find that solution, please let us know. i totally understand your pain. I love itunes however there are to many restriction for the money that has been spent, not to be able choose a few playlists on my P.C and have those SAME playlists sync to my MacBook Pro.


  4. While we are at it with iTunes sync rants, how about:

    1) Manual sync of music is way too cumbersome. If I have 100 artists in my iTunes list and want to sync all but 5 of them, I have to check off 95 boxes. Couldn’t they include a “select all” so we could then go back and de-select just the 5 we don’t want to sync?

    2) There should be an option for a “smart” sync that recognizes just the songs in your playlists and only syncs those, for those times when all you want to have on your ipod/iphone are the songs used in your playlists.

    If anyone knows shortcuts on how to do the above, please post.

  5. I totally agree with Bob’s comment about the check boxes! I’d love a select all option there too!

    As for synching, its always confused me lol even with my MobileMe. I just have’n’t really had the time to organize things properly either. I do have a MyWorldBook backup/storage device on our network at home now, it has an iTunes server and based on what I’ve read (haven’t set it up yet) I can upload my library to it and then anyone on our network (just me and my fiance) can access the music from either of our computers. I’m still learning how to deal with the technicalities of computer settings etc…but its good I should know how to do it.

  6. I manually manage everything I can possible manage in iTunes. I want full control over what I put on and delete as much as possible. The way I look at it is ……Would you have someone Automatically managing your bank account or would you prefer to Manually manage it yourself?

    1. Honestly? I’d rather have someone automatically managing both — bank account and iTunes. Automatic management also means pleasant surprises, especially when smart playlists pull in a few random tracks from your collection, just for fun.

  7. Terry, I have experienced many of your same frustrations with iTunes. This was my post from last year called “The messy, the missing and the mistakes: Adventures in iTunes Plus Upgrading” .

    I do have a software program to recommend called Syncopation. It can sync between different computers, including metadata, at the level of your whole library or specified playlists. It still doesn’t solve the iTunes Plus/nonplus problem but, hey, it’s a start. I wrote more about it in this review

  8. The whole iTunes lock-in frustrates me to no end. The worst is the 5 computer limt. Apple does not allow me purchase additional licenses for movies and videos. Why only 5? A couple of media centres and 4 family laptops puts us over the limit.

    1. Brian G, this certainly looks promising. I’ll have to give it a try when I get home and if it works, I’ll do a review here.

  9. iTunes has long seemed to me to be the forgotten product. We use it because there’s no other reasonable way to manage iPods and iPhones, especially if you like auto playlists and use your play counts and skip counts and other such stuff. But it really goes begging as a music library manager — it’s passable at best, because of this and many, many other frustrations.

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