back to article Fanboi primer: How to move your iTunes from PC to Mac

With Steve Jobs's world domination plan proceeding on schedule, I can't be the only iTunes user who wants to transfer my Windows-based music library to a Mac. For all the talk about the ease of switching to OS X, I've been unable to find any Apple-sanctioned way to take my playlists, song ratings, and number of plays with me. …


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  1. AlGodet

    How come did you get any problem ????

    I had the same "issue" about 3 years ago and did the move without a single hitch. I just moved the whole iTunes data folder from Windows to the correct folder (/user/Music/iTunes) on my Mac. Without any single problem. It was never even an issue for me : how have you been unable to do that ????

    Even better : I got from my switch all my Google Earth bookmarks and my whole Firefox and Thunderbird environments (including all my mails, of course).

    Maybe you should have stayed on Windows :)

  2. Anonymous Coward

    My way was easier

    Mate, I don't know about listening history because i don't use that anyway, but when I converted to the Mac at the time I just opened the directory in the Mac iTunes instead of an individual file and it took care of the rest. Everything imported and sorted just fine with no issues, music files album art and all the metadate I set up for compilations were honoured and everything sorted itself into the same folder hierarchy structure.

    Maybe it was a "just works" moment back then that does not exist now. Maybe I only had 90% of the work done for me and because I don't use other areas I didn't notice. But for most of us it was nearly a simple drag and drop and done as iTunes wasn't so feature ridden back then.

    1. tony

      similar experience, similar time.

      Did the same around 3 years ago, worked fine and just as easy only thing it didn't do was play counts and last played. But found an automator script which set them whole thing took me about 10 minutes + time it took to move 1tb odd of music and video.

  3. Mick F

    Wonderful but...

    I need the opposite "primer". Want to move my iTunes library back to my PC.

    Got rid of my Mini (crap machines) and will be getting rid of my MBP in the coming months. Tried Apple and happily moved back.

    1. Ty
      Jobs Halo


      Your fake post isn't fooling anyone. But if you DID have 2 braincells to rub together you would know that a Mini or MP make excellent Windows machines too. Poor soul.

    2. maclovinz


      "I need the opposite "primer". Want to move my iTunes library back to my PC.

      Got rid of my Mini (crap machines) and will be getting rid of my MBP in the coming months. Tried Apple and happily moved back."

      Posted on a Mac.

  4. Anonymous Coward

    You silly man

    You're missing the point. Why transfer anything? As a Windows (l)user, you had bad taste in music, but all that has changed now.

  5. Steven McAdam

    Alternatively... walk in to an Apple store with all your stuff

    Your article reminds me of how painful it was all looking whilst researching how I should go about consolidating the iTunes purchases from my 2 PCs (1 XP, 1 Vista), iPhone & iPad, along with the music I'd added to both PCs, on to my shiny new Macbook Air, and at the same making it host to both my iPhone & iPad.

    Not being particularly techie... yesterday I simply walked in to Covent Garden Apple store with all 5 devices, where a very positive & helpful young man (with a goatie) sorted it all out in about an hour, teaching me as he went.

    I left the Apple store happy. Their service is great, and they were nice to me despite my questionable dress sense.

    It's in stark contrast to my efforts about 2 1/2 years ago to get Adobe CS3 working on a shiny new Vista-based Sony VAIO. Despite spending 2 days on it, then finally turning up at Adobe's office in Uxbridge and begging (I wore a suit that day), I never did get it to work. I bought another (XP) laptop, and was stuck with the Vista one. I'm going to blow it up soon, I'll send you the video.

  6. Annihilator

    Possible fix

    I had a similar (may have been slightly different) error a while ago, and I found that deauthorising the computer, signing out of iTunes (all through the store folder), and then authorising again followed by a signin to iTunes fixed whatever knot the settings had gotten themselves into.


  7. Eddie Johnson

    At the Technical End of Things

    I'm just curious how much time the author spent trying to decide what band to "feature" in the article screenshots. I'm betting on hours of agonizing.

  8. bitten

    The Microsoft Way

    Why switch to Mac if it is to edit configuration files?

  9. Spoonguard

    I have a much simpler 2 step system

    1) On XP machine, delete itunes

    2) Reduce Mac to molten slag

  10. idothisdaily

    The Real Challenge

    I remember fighting with iTunes when I needed to use Windows on my Macbook.

    Bootcamp worked fine, but I needed to be able to read and write to the mac partition for iTunes to be able to use the one library of files, and that created many headaches, as there were a few little catches to doing that.

    iTunes isn't a bad product, but I sometimes do wonder what exactly the developers are thinking when they code some of their features in.

    That said, when i finally made the move over to MS only, everything moved perfectly;

    -Install iTunes on Windows

    -Find library files (should be in the default location)

    -Copy and replace equivalent from OS X

    -Enjoy muzac

  11. Anonymous Coward

    Yes, good tip.

    This is exactly what I did when I moved from a PC to a Mac nearly three years ago. It's easy enough just to drag the music files over but then you lose all historical data, playcounts, playlists etc. Editing the xml file with the new path is the only way I could find to be able to bring everything over.

  12. John Tserkezis

    A different angle.

    Why try to convert iTunes whatever to whatever else?

    Back when I had an iPod, I used iTunes (Windows) to configure it to appear as a normal drive, then completely removed the crapware suite it installed.

    From what I've read, iTunes Mac is halfway ok compared to the windows abortion, but either way, ANYTHING else is superior to iTunes anything.

    Mind you, "anything" else (and I've tried a few) wasn't fun to deal with, varying from just plain OK to downright painful, but either way, it was better than iTunes which was completely friggin useless.

    With half a brain and careful manipulation of ID3 tags, transfers worked out quite well.

    Both ways too, none of this never extracting from the iPod ever again bullshit.

    And just so this isn't an anti-apple thing, Windows media player is up to version 12, and still a complete abortion. What is it with media player/managers? Can no-one get it right?

  13. Kurgan

    Using non-drm and standard format...

    Simply copy all of your mp3, flac and ogg files from one machine to the other.

    Easy, isn't it?

    Oh, and I don't need itunes, too.

  14. Shocked Jock
    Jobs Horns

    iTunes? Forget it!

    My experience with iTunes on Windows convinced me that Apple could not organise software on that platform, and would be unlikely to have the savvy to organise it on a BSD-based platform either (although Apple's conversion to a real, as opposed to an insanely proprietary, platform is welcome).

    Revising files under arbitrary labels, such as music instead of user-allocated ones, losing album art and/or replacing it with obviously wrong alternatives, losing details carefully entered repeatedly - you name, iTunes did it. So I gave up, and now my recordings are in the bright new world of Android, with files moving easily between that and, dare I say, Windoze. Simple file management allows me to change details - and they stay put! What a relief to be shot of that pile of Jobsian turd that is iTunes.

    1. Michael C

      Understanding, you lack it

      The issues with iTunes on Windows have little to do with Apples coding ability, but with NTFS.

      On a mac, the metafile data for each iTunes object is stored in a file header that is part of the HFS+ file descriptor. This metadata is stored inside the file system database as well as in the file, so disk access time to "get info" on files is extremely small. On Windows, that metadata is a part of the file itself, requiring the file to be opened in order to capture album art from it. This creates a massive amount of disk activity as you move through your library. Also, the structure of the iTunes database itself is slightly different, leading to a larger XML data structure on Windows than it is on a Mac, causing additional lag and memory utilization especially on very large libraries. These are not issues apple can work around on a PC until Microsoft replaces NTFS with a modern file system.

      Microsoft gets around this issue (to a limited extent) in WMP by a) not loading album are for the entire library and only showing it when a single song or album is selected, b) not making full use of song meta data outside of the ID3 tag, thereby requiring a secondady database containing actual data other than song location, rating, and play count (which can be corrupted), and c) ignoring such features as dynamic playlists or playlist-by-association (genius) in favor of simple "filtered" playlists or manually created structures, eliminating most if not all the intelligence that could be used to make large library management easier.

      Blame the source, not the scapegoat.

      1. Wibble

        NTFS has extended attributes

        Just a small point, but NTFS always has had extended attributes that can be used to stash metadata/whatever.

        Maybe it's because iTunes on Windos needs to work on FAT as well as NTFS; just create a single code base that works on all file systems? If they exploited NTFS, they'd still need an alternative for FAT; conversely if the FAT version works on NTFS, why bother building for both?

  15. Anonymous Coward


    You could start by trimming your music library. Mine's bloated enough at 8,000 songs (= 26 days of music), but 50,000? That's 140-odd days assuming an average of 4 mins per song. Too much, too much. Rating / playlisting and otherwise sorting that much music is not appreciation, it's a combination of hoarding and OCD.

  16. Anonymous Coward
    Anonymous Coward

    Fortunately, I had a more modest library

    And more modest needs (I just want to listen to my music - no rating, history and shit like that) so for me, it was just a matter of moving the folder from one location to another. Bizarrely for me, there are a couple of vids on my iPhone I can now only get to by searching for them and a couple of albums disappeared and then reappeared after the next iTunes update (and thanks to the "everything just works" mentality of the Jobsian Cult, getting support for obscure issues is not always trivial)..

  17. Anonymous Coward
    Big Brother


    Just hope there's numerous Dan Goodings in the SF area, or he's got all the receipts.

    Otherwise it looks like he's shouting "coo-ee - RIAA! Over here".

    1. Michael C

      not unreasonable

      I have 40,000 songs. Every track legally obtained. Starting with about 650-700 CDs (the total lifetime collection of my wife, myself, plus some given to us by friends who didn't want them anymore), got me to around 12,000 tracks. I've purchased about 500 sings directly since, plus the free Tuesday tracks every week going back years.

      Then there came Stream Ripper. Tune to a shout-cast station (or other similar feed) that broadcasts "space" between each track and let it run for a few days. It automatically separates the files and names them based on the track titling, and detects and deletes duplicates. For a while i was ripping 4-6 concurrent 256bit feeds, adding half a thousand new tracks a day. It is not illegal to record a broadcast that is free to receive. Modern stations limit easy record-ability by using voice-over, cross fade, etc, under pressure from the RIAA, but in my music preferences, I could care less about Pop and Top 40, so finding stations that ignore RIAA requests to limit recording is easy.

      I've not run it in a while (after a few weeks, finding new tracks becomes less and less frequent), and it;s probably time I turned it on again. I run it a few days once every few months and catch a few hundred new tracks, but finding good stations is harder and harder to do.

      Anyway, 40,000 songs is far from improbale, or impossible, to do legally. Hell, i know some people who have bought 2-3 new CDs every week since the mid 90's and could legally own that much music through purchase alone.

  18. squilookle
    Thumb Down

    99% of the music played in my house is through Spotify these days.

    I spent about 10 years trying to maintain a large library of MP3's, moving them from computer to computer every time I upgraded, and I can't be arsed anymore. That library now lives on a hard drive in a drawer somewhere around here.

    None of this was on iTunes. I did briefly try iTunes once or twice, I didn't like it.

    1. MineHandle
      Thumb Up

      Wish it was available here...

      Even though we there is supposed to be an "open market" in the EU, spotify is not available here.. boo!

  19. Anonymous Coward

    Possible fix

    Open the .itl, and delete it's contents. Leave the blank file in place. Start itunes up with the .xml present, and it'll bitch about the library being corrupt or somesuch nonsense, and rebuild the .itl file. That should cure the error.

  20. An_Old_Dog Silver badge

    Lesson Learned: "don't use proprietary / overly-complex data formats"

    When the company owns the format your (meta)data goes into (or if the format is sufficiently complicated), you no longer own your own (meta)data.

    1. Michael C


      I didn't know ID3 and XML were proprietary formats...

      Gee, guess i can't use WMP either, or WinAmp, since they also maintain their own database.

      Look, the data in the song file is in standard formats. The data in the database only matters to the application. Ratings and other metadata are not part of the file *(they can be, but only in optional or otherwise non-standard fields equally not cross application compatible).

  21. Ivan Headache

    I was thinking the same thing.

    When I had 300 or so LPs It was hard enough to decide what to listen to. 50,000 tunes is a bit ridiculous.

    I have just over a tenth of that number (all legit), they occupy about 32GB of space, and according to iTunes, will take 51.6 days to listen to in entirety.

    It's the same with those clients I visit who have 10,000+ photos stored in iPhoto or whatever they use (and there's plenty of them). What are they possible going to do with 10,000+ pictures? Looking at them will take over a day at 10 seconds per picture - and that does count the 200 or so extra they appear to add each week.

    In the old days, if the average Joe took more than 24 pictures in a month he was probably a professional. Now it appears to be the daily norm.

    1. Havin_it

      You are Ebeneezer Scrooge AICMFP

      I'm sure you didn't mean it that way, but I can't help finding something terribly curmudgeonly about your post. And I say this as someone who's probably nearer to you than Drew Cullen: I have as many mp3s as I could be arsed to sit around ripping and tagging CDs for, and the dozen or so photos per year I considered worth taking with my phone are still on my phone until I hit capacity probs.

      Yet I rather envy Drew with his 50,000 tunes, especially if he actually likes most of them. I'm guessing he's a religious album-ripper: rips the whole thing for completeness, and because y'know, one day he might come around to liking one of those other tracks. He can just hit Shuffle and go for a wander through the dark corners of the collection for as long as he likes, and it's sure to turn up the odd forgotten gem.

      This and the photo collection are much the same: no matter how big it gets, you'll have made a note of where you put your favourite stuff when you added it - which is why a capable and transferable cataloguing system is so valuable. If you have a lifelong passion for something, be it music or photography or lead soldiers, the collection may keep growing as long as you live, so there is no "too many".

      (Full disclosure: I'm a librarian's son)

      1. Anonymous Coward
        Anonymous Coward

        Re: You are Ebeneezer Scrooge AICMFP

        Hey - I have less than a thousand songs on i-Tunes!

        Did you mean Dan?

    2. tony

      50,000 songs,

      Welcome to the world of random playlists, with a few choice selections you can't travel without.

      It's a nice feeling when some old Gem you've forgotten about turns up

  22. Steve 114
    Thumb Down

    Bad Taste

    in so-called 'Songs' remains bad taste whatever hardware they're on.

  23. Reginald Marshall

    Editing a huge text file?

    How very... Windowsy, when a lowly sed script on a Mac will do the job nicely.

    1. Some Beggar

      Ri-i-i-ight ...

      ... because SED (or AWK or perl or Emacs or any of the other bajillion simple editors) are only available on Macs.

      1. Michael C


        no, because so few people on windows even know what they are, let alone go through the trouble to install the right binaries and a bash emulator.

        1. Some Beggar

          But at least they'd know that you don't need a bash emulator for sed.

          Number of people in this office fluent with sed and similar tools: 43

          Number of people in this office using Macs: 1

    2. Breezedave

      Windowsy find and replace

      It may seem windowsy and a bit archaic, but as long as you use a text editor that waits until all replacements are done before refreshing (like notepad 2) it can be pretty nippy too.

      I should know, I used to have to maintain a 1GB database at work that was stored in a text file (don't ask).

  24. Zot

    50,000 tunes, you must be rich!

    How can you possibly afford so many songs!?

    Oh wait. Time to ring the feds... .. .

    1. Anonymous Coward

      50000 tunes?

      It sounds like a lot, but I have an MP3 collection that consists solely of CDs that I own and have ripped to make them easier to listen to. All the CDs sit in big boxes in storage. That has 25000 tunes on it. Probably a couple of thousand CDs in total. Over 20 years of buying CDs that is only about 100 CDs a year.

      On a separate note. I thought Macs were "it just works" not "it just needs a bunch of hacking of config files, then it always errors every time I use it".

      And I've heard nothing buy bad things about iTunes. Personally, I organise my music on a SqueezeServer, but then I don't like mobile music because of the poor sound quality on headphones.

  25. Michael Xion
    Thumb Up

    iTunes error message fix

    Had the same problem. Just turn Genius off under the store menu then turn it back on again. problem should be fixed.

  26. Anonymous Coward

    In todays news...

    How to move your Ipod content back to Windows, since iTunes completely screwed up your directory structure, massacred your tags, destroyed your sorting and you now seem to have a seperate album for every song, bar the albums that seem to contain every song thrice.

    But the writer of this article will find all of this out very soon. I shall be looking forward to the assorted expletives in the follow-up articles.

  27. teapot9999

    Transfer iTunes library

    Just turn on Home Sharing on PC and MAc and iTunes will copt everything for you.

  28. Barry Lane 1

    Ooh, an opportunity

    for PC fanboiz to tell the world that they think Apple is crap. Says a lot about the PC fanboiz, frankly.

  29. Anonymous Coward
    Anonymous Coward

    God, listen to you bunch of whiners!

    I also made the switch between Windows and Mac (mostly because I got a second-hand MacBook as a gift when my old Toshiba was on the fritz), and frankly, it was easier creating an empty library in iTunes and dragging and dropping my 28GB of music (and yes, I listen to it regularly).

    The bit that did take the longest was iTunes wanting to analyse the sound leveling characteristics of the songs, but the album art was no problem at all (but it did leave some out which I modified myself after), neither was Genius (I didn't get the error).

    When your music lives on a Windows network drive (like the bulk of mine does), it's just as easy... drag and drop. Done. That said, iTunes on Mac is faster than on Windows - Fact. It responds a lot quicker than it ever did on the Toshiba.

    Moving back to Windows shouldn't be a problem either. If you can't be bothered with exports, imports etc, just recreate your library in Windows and drag and drop the files. It'll be slower (Windows), but it'll work.

    And just to add a disclaimer... I am not a fanboi, won't ever be. I treat Mac with the same cynicism as I do Windows, or any other OS for that matter.

  30. Matthew Flint

    Genius disabled

    I've had Genius disabled ever since it recommended "The Very Best of Chas and Dave". I was not amused...

  31. Anonymous Coward

    There are easier ways

    I haven't read all the comments so far, so i may be repeating what someone has already said but I think there is an easier way.

    This is how did it just very recently:

    You have to make sure iTunes has consolidated your files - go File|Library|Organize Library and check the two check boxes.

    Then copy the iTunes folder to your new machine (in the default location is best). Then you just have to start iTunes on the new machine while holding down the Option key (or shift in windows). It then asks you to choose a new library, and you select the folder you just copied.

    it's explained far better here:

  32. Anonymous Coward


    Typically the Windows users seem to still think by slating the Mac 'fanbois' they are cool(?)

    Notice: This isn't 1998 anymore alot of people use and like Mac.

    Hence why flame comments are being rated down...

  33. Neal 5


    Not an AmeriCAN.

  34. Michael C


    Wow, this not only isn't hard, there are multiple ways to do it. This is a rant flare for PC Fanbois only, and not actually a real issue at all.

    Option 1: Consolidate library on PC; copy library to Mac iTunes default folder locations; launch iTunes holding down option key and select library file; wait while itunes imports the PC library file into a Mac library file.

    Option 2: turn home sharing on for both machines. Allow automated copy process to complete. (optionally, remove iTunes authentication from PC when u r done). Note, this only moves files purchased through iTunes to the new machine.

  35. Anonymous Coward

    Planning in advance?

    1. Stop storing on a single machine for a start!

    2. Stick them on a NAS or net-shared system. ( I have a couple of 4.5TB ReadyNAS systems. )

    3. Simply re-point to the netshare whenever you need to access the music from any iTunes enabled type device.

    I have 4 Macs and a two PCs at home and none of them store any iTunes data, it's all on the network.

    I have three separate iTunes libraries to maintain. Mine has 35,000 tracks, my wife's is 21,000 and my kids a small 2,500 tracks. All kept separate and all secured from one another. Anyone wants access to anyone else's, simply enable iTunes sharing and you get instant access to anyone else's library. Even the media-centre Xbox can access all the libraries and blast music through the home cinema, by simply accessing the iTunes directories through CIFS shares. ReadyNAS box allows you to share the same data over several different protocols at the same time. 18 months and no problems yet, touch wood.

  36. Stevie


    Does moving this lame piece of software onto it's home turf make it any better at finding cover art when you copy a CD into it? Or (be still my beating heart) having found a picture, make it any better at figuring out if it is the *right* cover art for the album by that artist?

    I have so many squares with question marks in them (You couldn't find the cover art for Bryan Ferry's "Taxi"? Or Gabriel's "Ovo"? Or Bowie's "Scary Monsters"? Really? ) it makes a mockery of the visual display.

    Funnily enough, Windows Media Player seems to be able to find more of the covers even from the same library. Not all of them, but many more than iToonz.

    Go figger.

  37. welshman10

    Re: 50,000 Tracks, How Do You Know What To Listen To?

    It seems some people need to be introduced to Smart Playlists. Just like listening to the radio, but can be configured to only music you like and/or haven't heard in a while. Oh and no annoying DJ voiceovers or ads.

    Only thing I don't like about itunes is the fact the last update removed the "Reset Skip Count" function...a bizarre decision. This was a handy function I used from time to time for fine tuning smart playlists. Besides that, itunes is the best music player around if you know how to use it.

    All it needs is the Reset Skip Count function restored, the ability to add avi/divx files to the video library and the ability to rate videos on the ipod touch and it will do everything I want from a media library.

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