iTunes 10 on Windows Server 2003 (or Home Server)

Have you been wondering how do I install itunes 10 on a Windows Home Server or Windows Server 2003?

My office recently bought an iPad and we wanted it to sync with our server, running windows server 2003. Problem was during the install of iTunes 10, i got an error… “apple mobile device support failed to install”… The install would complete and everything worked, except when i plugged in the iPad… it would not connect / sync with the server.

I searched the interweb’s and found a few solutions… the easiest (that worked for me) is below… we basically have to manipulate the install of itunes so it does not check the operating system and fail at installing the “apple mobile support”… it sounds tougher than it is, but its actually relatively easy if you are comfortable with installing a few small free programs… this should work with Windows Home Server as well, seeing as its built off of Windows Server 2k3… The steps to do this are Below

Install iTunes (it will complain about the Apple Mobile Device Support, we’ll fix this next)

1. Separate the iTunes install files so we can manipulate the Mobile Device Support install.
1a.Download the latest iTunes install file here iTunesSetup.exe.
1b. Download and install the latest Win-Rar here to separate the install files.
1c. Once Win-Rar is installed right click on the iTunesSetup.exe and select “Extract to itunesSetup (this will create a folder right next to the iTunesSetup.exe, in this folder you should see the file we want to edit “AppleMobileDeviceSupport.MSI”

2. Edit the install files with Orca
2a. download the MS software development kit here
2b. IMPORTANT! Click the install for the MS SDK kit and keep clicking next until you see the screen shot below… un-check everything except for the Win32 Dev Tools.. (that way the install is just 32.6-MB rather than 1.2-GB

2c. Once it has semi-installed/downloaded the SDK, navigate to C:Program FilesMicrosoft SDKsWindowsv6.1Bin and double-click on Orca.msi… this will install Orca….

3. Edit the iTunes install file
3a. Go to the start menu and locate and launch Orca
3b. Drag the “AppleMobileDeviceSupport.MSI” file we extracted in step 1c. to the Orca window

3c. Click on the “LaunchCondition” in the Tables pane then right click on the row that says “VersionNT =501 And Service Pack Level >=2….” in the condition window… select “drop row” and confirm you want to remove it permanently (this is shown in the screen shot)
3d. go to file, and Save the AppleMobile DeviceSupport.msi with this change we did
3e. double click the AppleMobile DeviceSupport.msi and install it, and then double click the itunes.msi and repair the install.

UPDATE: A commenter below mentioned that with the latest iTunes install files you need to not only edit the AppleMobileDeviceSupport.MSI as mentioned above, but the iTunes.msi in the same manner, as that now checks the OS as well at install.
Thanks MC.

This should install it without any errors, and you should now be able to sync your iPhone, iPod, iPad, iWhatever to your Windows Server. On a side note when I restart my servers i get an error message about iTunes help files not loading or something, but iTunes and syncing functionality still work fine.

53 Replies to “iTunes 10 on Windows Server 2003 (or Home Server)”

  1. Doesn’t appear to work for me with iTunes I follow the instructions line by line, but on the last step, repair install of itunes.msi, I get Service ‘iPod Service’ (iPod Service) failed to start. Verify that you have sufficient privs to start system services. A Retry brings the same error, I can click Ignore to complete the installation.

  2. mmm… I’ve heard some people having trouble with this even with an OS officially supported by the software… I’d try I few things if ytou haven’t tried these already…
    1. make sure your logged in as administrator
    2. Try and re-download / re-install again
    2. See if you can manually start the service via runnng Services.msc if it still fails
    3. Temporarily disable your fire wall and try to do the install again to see if the firewall is creating some type of permissions issues

    let me know if any of these works or doesn’t

  3. No dice. I’m logged in as Administrator, turning the firewall off doesn’t appear to make any difference. Trying to manually start the service results in Error 1053: The service did not respond to the start or control request in a timely fashion. I’ll give it one last go with the new release … Thanks for your help, shame it doesn’t seem to want to work.

  4. This worked for me, however, the latest iTunes installer (10.x) checks for the version of windows as well. I dropped that line from the itunes.msi as well. iTunes then installed just fine. Thanks for the quick tutorial.

  5. Love this. Because I wanted to stream to my apple tv, I found that I also had to remove the same line from bonjour. Ended up just removing that one particular Launch Condition from all of the files.

  6. Ive searched this huge thing we all call the internet, and I have found no solution for my problem, my problem isn’t with installing iTunes, but when I go to run iTunes, quick time fails to initialize error (-2906) everyone says it seems to be a compatibility issue. I have tried a lot to make this work, I’m running windows server 2003. I thought this might have helped me but it didn’t, it was a very nice tutorial though. Good job. If you know how to fix my problem, please it would be much appreciated if you could throw some advice my way 🙂

  7. Brian, I’d make sure you were logged in as administrator when you installed everything, and if you were, try doing a power cycle of your machine to clear any permission issues with the install directories that might have occurred during the procedure. If you are unsure who you were logged in as I would uninstall, powercycle to clear the registry, and re-install logged in as administrator and hopefully that is all that is wrong. Good luck

  8. Justin, I’ve had quicktime installed on my server2003 for quite a while now, even before I installed iTunes and wrote this tutorial. So I know it can work with server 2003 without any modifications, or at least it did.

    However, I found this on some apple support forums, don’t know if you came across it or not in your searches, but hopefully it helps you… They say one resolution to that quicktime error 2906 is to turn off Compatibility Mode for QuickTime.

    1. Right-click on the QuickTimePlayer application (located in C:Program FilesQuickTime) and choose Properties from the shortcut menu.
    2. In the Properties window, click the Compatibility tab
    3. Deselect all checkboxes currently selected in the Compatibility tab.
    4. Click Apply.
    5. Close the Properties window.

    Note: If QuickTime wasn’t in Compatibility Mode, verify that iTunes isn’t in Compatility Mode using this article.

  9. Thanks Bob, I checked & I am logged in as Admin & I did try to reboot after the install. I have since uninstalled & will re-try to make sure I didn’t miss a step.

  10. Still no luck I dropped the Launch Condition from “all” the .msi files via orca. Still getting error message that iTunes is being used by another user & is unable to open?? Any one have any idea?

  11. Tim, thanks very much for the tip on how to get this installed. For reference I run Server 2003 Standard R2 x86.
    This worked great but there were a few extra steps I had to perform:
    1) Remove the “VersionNT =501 And Service Pack Level >=2….” from each and every extracted *.msi that contains that line under “LaunchCondition”. Just hit “Save” in Orca to re-save these edits back as the original file’s name in your “iTunesSetup” folder. IOW, don’t save them someplace else and don’t rename them when you save.
    2) Close all running versions of Apple software. (iTunes, QuickTime, etc.)
    3) Stop all Apple/Ipod services (run services.msc to accomplish this):
    Apple Mobile Device
    Bonjour Service
    iPod Service
    4) Uninstall all prior versions of the following from “Add Remove Programs”:
    Apple Software Update
    Apple Mobile Device Support
    (NOTE: My attempts to run the remover for “Apple Mobile Device Support” always threw an error so I downloaded msicuu2.exe and used it to remove this item.)
    5) Rename “%ProgramFiles%Common FilesApple” to “%ProgramFiles%Common FilesAppleOld”
    6) Go back to your “iTunesSetup” folder and double-click “iTunes.msi” to run the complete installer.
    Everything installed perfectly for me and ran without error.

  12. Many thanks for your help! It all worked exactly as described.

    I’m in the unenviable position that my iPod won’t work with iTunes 10 (due to the widely reported -and widely ignored by Apple- issue of the seemingly random free space calculations, which keeps refusing me to add new material even though there’s plenty of gigabytes left!), and that my iPad (at iOS 4) won’t work with iTunes 9!

    So I was VERY glad to find this manual to be able to install iTunes 10 on my server for my iPad, while keeping iTunes 9 on my PC.
    I swear I’m ready to pack in the whole Apple thing altogether…

  13. haha matinjn… sometimes i feel like that as well… I remember reading something like… “apple products are not meant to conform to you… you are meant to conform to apple products”

  14. thanks for the tips Tim. i’m in the same boat as Justin. i did the edits just like you suggested first, and the Quicktime application won’t run. Compatibility is set exactly like instructed and still no dice. Then i tried the way Bryan suggested, and still unlucky. Any ideas? Anyone?

  15. Just tried this. I get stuck on itunes install, validating install. It just sits there for ever trying to validate. I’ve tried pre installing Quicktime then running itunes as stated here. But no dice, install gets stuck “validating install”.

  16. Hi All,

    I’m trying to install iTunes 10.2 in Windows Home Server (HP MediaSmart EX490). I’ve tried everything in the thread above and, although the install has now moved past the mobile device support error, I’m now getting a quicktime install error – The installation of quicktime did not complete successfully. iTunes requires Quicktime.

    Its really strange because I can install the latest version quicktime on its own using the download from Apple without any problems at all.

    Any support would be much appreciated.


  17. Hi Martin,

    Follow the procedure above and before you save the file in step 3d click on the “caPackage” in the Tables pane then right click on the row that refers to quicktime and drop that row. That should stop quicktime being installed by the itunes intaller, you will need to install it independently though.

  18. Hi there,
    i’ve tried to install iTunes 10.2.1 and it failed. my google search linked me to this page an it works great! Now i can share all my music directly to my ipad iOS 4.3!

    Thanks and best regards from germany!

  19. Thanks for the info. I think is not necesary to install the modified AppleMobileDeviceSupport.MSI first, so directly click on the iTunes.MSI and all must go well.

    I tested this with srv2003 enterprise sp2 without a previous installation of itunes.

    Best regards from Spain.

    1. Just used this procedure to install on WS2008 R2 Standard running as a VM w/Hyper-V. Simultaneously feeding video to three A-TVs.

  20. I’m not able to get Itunes 10.3.1 to install because I get a quicktime install error – “The installation of quicktime did not complete successfully. iTunes requires Quicktime.”

    I tried to look for the “caPackage” in the Tables pane as Jon suggested above, however this table is no longer present in Itunes 10.3. Any idea how to disable the installation of QuickTime?


    1. I was able to get it to install by dropping “QuickTimeInstallFailed” and “QuickTimePreInstallMSIProc” under the CustomActions table for the Itunes.msi. Then i installed QT after iTunes was installed.

  21. I saw this article back in december, finally got around to trying it. Tim’s original instructions worked perfectly for me with the latest version of iTunes 10.3.1 on an HP EX470 Series Home Server with Version 3.0 Upgrade and the 1GB Ram installed.

    I was previously syncing my iPad and iPhone thru my PC iTunes. My iTunes Library including itunes folder resides on my HP Server. So it had to transfer everything back and forth via my network when I plug a device in. It’s substantially faster to plug into the USB of my HP Home Server and sync to iTunes vs. my PC thru my network to sync to my HP Home Server iTunes Library. Clear as Mud? =)

    Plus, my HP Home Server is always on, I use my PC less and less these days, we have laptops and iPads in the family that all use the HP Home Server to access content..

    Thanks for the post Tim!

  22. Great tut, I get it installed fine on my WHS V1, no errors until I connect my Nano 4th Gen then I get the error “An iPod has been detected, but it could not identified properly.”
    I have rstarted the machine and iPod Services several times and read all the above.
    Any help would be appreciated.

  23. Craig – great tip on using iHomeServer; exactly what I wanted for getting iTunes to start automatically instead of me having to login each time the computer boots – thank you!

  24. Thank you for this, it saved the day. I love my MSmart WHS and running iTunes on it has been great (except for sound card warning which I just ignore).

    This fix worked like it should, installed fresh iTunes 10.5 running WServer 2003 sp2. BTW – you don’t need Quicktime anylonger with 10.5 I deleted 10.4 and Quick Time before 10.5

    Now i need to check out iHomeServer to help manage iTunes.

    I ran into a problem dowloading the SDK and Win-Rar, trick is you need to go to add remove programs>window components>uncheck user security, make sure you save settings and close out of IE then go to site, download app then re-enable security settings (i guess this is a good idea).

  25. Thanks a lot for the instructions: I just used them to successfully install iTunes on the latest version of Windows Home Server.
    When iTunes Match is released I hope the same process will allow the new version of iTunes to be installed on WHS, too.

  26. Just to note: jTunes does the same thing iHomeServer does, and it’s free…..

    Thanks for the tip about only needing to do the MobileDevice MSI file… iTunes 10.5.1 installed perfectly on my HP MediaSmart

  27. Sorry, one more tip to share…. searching Google for “orca.msi” will bring you to SoftPedia to download *just* orca.msi, which is an under-2-meg install…. no jumping through hoops on the Windows SDK to get only it installed

  28. Worked PERFECTLY…I also had to upgrade the server from 1.1 USB to 2.0 so I thought the problem was with the new install. Tested around and found it was working fine so I went on to this problem and found your solution.

    Without any hitch, everything appears up and working fine with no errors. I have not rebooted the server yet….

    Thanks 10 million time over 🙂

  29. FYI – was browsing the iHomeserver blog yesterday and they’ve posted a free tool that does a single-click iTunes install on WHS v1. I just tried it and it installed iTunes without a hitch. You download their tool, run it, point it at the itunessetup.exe and then it appears to do all the MSI patching behind the scenes so I didn’t have to install orca or the SDK. I then proceeded through the iTunes install and then I didn’t get the “requires SP2” error that i was getting before.

    Here’s the link

  30. Huge. Thanks very much. It helps to read the comments to this post (just go get Orca rather than d/l’ing the SDK) but a big THANKS for this in any case.

  31. Would this be valid for any of the x64 editions on WS 2003 ?
    Also has anyone tired using the tool from the iHomeserver blog to do an install on WS 2003 instead assuming the architecture is similar ?

  32. Thanks for this info., Got itunes installed on my HP Mediasmart 495 home server, but while able to “Add folder to library” and get my music added, when I try to do the same for my movies, the first time I try this action I get a fleeting message that makes it look like the process is starting, but then it immediately stops and my movies are not added to iTunes. If I try again, I don’t even get that indication that anything is happening…
    What am I doing wrong? How can I get the movies to ITunes as that is what I’m much more interested than streaming than the music (the music files are small enough to be on my ipad/ipod, but I’d prefer to stream than be constantly transferring movie files to the peripheral devices?

  33. Great Tutorial, got a couple errors at the end but after installing the rest of the extracted installs from ITunes.exe it worked great!

    OS: Windows Home Server Build 3790
    ITunes (Newest Version)

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