My previous post here detailed how to install iTunes on Windows Server 2003, however since the latest update from Apple, iTunes 9, this fix/ hack doesn’t necessarily work, especially from my experiences.
Click continue reading to find out how to install iTunes 9 on Windows Server 2003/ SP1/ SP2.
Most of the problems stemmed from iPodService.exe, a service that automatically detects your iPod/ iPhone when plugged in, and then can automatically launch iTunes for synchronisation. Even if you don’t want to enable this activity by default, as will probably be the case on a server, there is no option for omitting this during installation of iTunes 9, or indeed previous versions.
Symptons
During installation, or upgrading to iTunes 9, quite near the end of the installation, you encounter an error indicating that the iPod Service cannot start due to possible permissions problems or something else similar. What actually is happening is that iPodService.exe is being started, but as the new program is incompatible with Windows Server 2003, it immediately crashes, and hence the installer thinks that it isn’t starting.
You can verify this by navigating to the iPod installtion directory e.g. C:\Program Files\iPod\iPodService.exe. With the Windows Task Manager open, sorted by name, scroll down to names starting with ‘I’. Then click and run the iPodService.exe manually. You will notice it runs momentarily, but then crashes. A quick look in the event viewer and this will confirm there is a problem.
Resolution
- Before installing iTunes 9, and whilst you are still using iTunes 8, shut down iTunes, and all iTunes related services. The easiest way of doing this is to open the Windows Task Manager and ending the processes of every iTunes program/ service. iTunes.exe, iTunesHelper.exe, iPodService.exe.
- Navigate to C:\Program Files\iPod\. In here COPY all files to a temporary directory called v8. You will need to copy iPodService.exe file and iPodService.Resources folder.
- Following my previous Installing iTunes on Windows Server 2003 post, modify the .msi files to allow the installer to run on a Windows Server. (Otherwise you will receive errors like “this program cannot run on this operating system”…
- Run the installer for iTunes 9.
- When the installer fails, relating to the iPodService problem, navigate to C:\Program Files\iPod\, CUT the iPodService.exe and iPodService.Resources items and paste them in a folder called v9.
- Now open the v8 folder, COPY all the files, iPodService.exe and iPodService.Resources into the root of the C:\Program Files\iPod folder. (Replace the v9 files if you didn’t CUT them.)
- Now click retry in the installer.
- Installer finishes.
- iTunes 9 is installed!

Known potential problems
- As far as I am aware this fix does not allow iPod/ iPhone connectivity to this computer. This is because the v8 version is incompatible with the v9. I could be wrong though? Update someone has pointed out to me that they are able to connect their iPod to the Windows Server after this.
More Help
If you encounter any sort of problems with this fix, please use the comment system below, and I will try to reply and help you. I cannot make any promises. Please give a valid email address so that I can reply to you.
Disclaimer

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I’m running 32-bit Windows 2003 SP2 (not Windows 2003 R2, fie upon it).
Anyway, I just did the iTunes 9 install (upgrade from 8.x, actually) following a lazy version of these instructions:
1. I quit out of iTunes 8, but did not kill the other iPod/iTunes procs.
2. I edited all the MSIs (deleting NTVERSION LaunchCondition entries), but only double-clicked on the iTunes.msi installer (figuring it would launch whatever else it needed to).
3. I did not swap the v8 version of iPod service back in.
4. Restarted computer
iPodService started just fine.
Launched into iTunes 9 & plugged in my iPhone. Recognized it correctly & sync’d correctly as well.
Plugged in a 1 year old nano. Recognized it correctly & sync’d fine too.
Plugged in a 4 year old nano (the tall & thin “flat” one, before the fat year, and before the rounded metallic ones that are now current). Recognized it correctly & sync’d fine.
In other works, everything is working perfectly. The iPodService.exe file that I’m running is 9.0.0.70, which is the new one, and it seems to work fine.
Maybe the issue (if any) with iPodService is for 64-bit Windows installs?
Strange, I tried on numerous occasions on getting iTunes 9 to run on my Windows Server 2003 (SBS) SP2 (32bit), and it always failed at the part where iPodService.exe starts. No matter what I did, install the seperate MSI’s, repair the iTunes 8, restart the Server….nothing worked.
I did a quick Google to find that others have experienced the same problem.
I followed their instructions, added my own steps, and solved my problem, and then subsequently wrote these instructions on my Blog.
It is great that it is working with you. Strange though how it works with some and not others. The MSI edit is definitely required though!
Cheers,
An alternative technique is to drop the ServiceControl and ServiceInstall tables
from the iTunes.msi file.
Also remove the InstallServices and StartServices from InstallExecuteSequence.
What if you did a complete uninstall of itunes 8 before reading this post?
You’ll need to reinstall iTunes 8 for a copy of the iPod service folder, save this somewhere safe like your desktop, upgrade to iTunes 9.1 etc, and then replace the iPod service folder (v8) with the v9 one, and then continue with the installation.
I followed the file copy procedure above and the install finished. I did find that the first time itunes 9 started it tried to reinstall ipodservice, which of course failed like before. Copying over the v8 one and hitting “try again” worked like a charm.
Regarding v9 iPodService.exe not running, this is just a service rights issue – easily sorted!
As described here edit the AppleMobileDeviceSupport.msi using Orca to remove the OS check. I don’t think it’s neccessary to edit the other MSI files as yet, well I didn’t!
Run the iTunes v9 installer itunes.msi
When it stops with the error message about permissions, launch services.msc from the Run option on the Start Menu. Find the ‘iPod Service’ and open it’s properties sheet. On the ‘Log On’ tab, change it from a ‘Local System Account’ to the Administrator* Account and enter the password for that account.
Manually start the ipod service, then click ‘Retry’ button on the permissions error message that started this nonsense. It will go through and iTunes will complete the installation.
* For security this should really be another account rather than the all-system encompassing do everything main Administrator account – but no other account here seems to work. Could someone please find out why?
Richard’s recommendation to remove the ServiceControl, ServiceInstall, InstallServices and StartServices tables from InstallExecuteSequence (from the iTunes.msi file) worked perfectly for me (Windows Server 2003 R2). I’m not sure how Richard decided to do this but I did it with a free MSI modification program called ORCA which is easier for me to do then using an “.mst” file with the msiexec command. Don’t forget that you need to remove the Launch Condition entries too.
I got a clean install of iTunes 9.0.1.8 to work this way. It recognized my iPhone too. Also – don’t forget that in Windows 2003 to get an iPhone working with the Scanner and Camera Wizard you need to go into Services and start the Windows Image Acquisition Service (WIA). This service is normally disabled in Server 2003.
Hi, Any reason the iTunesHelper fails with error code/Window “itunesHelper was not installed correctly. Please reinstall itunes Error 7″.
When I use Orca and look inside the MSIs they say error code 7 is {{Disk full: }}. Am I looking in the right place?
I’m presently connected directly to the server (the iphone is) and ultimately I’m trying to connect to the server via a remote desktop session and connect to Outlook and sync the calenders to my iphone. If you see any issues, I’d also appreciate hearing those.
Cheers
It sounds as though your hard drive space has reached a critical low level accroding to when you use Orca. Verify this, uninstall iTunes, modify the msi’s with Orca, and reinstall iTunes.
If you are doing this with remote desktop on an iPhone – then good luck – getting a bigger screen and more contorl over the keyboard and mouse would be better in this instance.
Hi,
I have followed the instructions from the previous post and modified the iTuneSetup
.msi files accordingly. When I’m trying to run iTune.msi, I get an error code 2229.
Any idea, what I’ve been missing? Prerequisites?
HW: HP nx8220 notebook
OS: MS Windows Server 2003, Standard Edition, SP 2
Günther
Hi, It’s hard to know what is going wrong. I would start from scratch if I was you. Uninstall iTunes from your system and then restart your machine. Then download a fresh copy of iTunes from the website. Once the download is complete, extract the download using something like WinRAR to get each component .msi file. Then use Orca to modify the Operating System requirement and follow the other posters to modify the ServiceControl options too. Then run the main iTunes.msi intall. Run through the install and hopefully all will be okay!?
I upgraded from itunes 9.0.1.8 to 9.0.2.25 (I use Windows Server 2003 R2) and after the upgrage I now get the “itunesHelper was not installed correctly. Please reinstall itunes Error 7″ error message that Optin got. I’ve got gigs of space left so I don’t think the error relates to available disk space. Still, my iphone seems to sync ok anyway except it hangs if I try to sync photos. I had the hangs on photo sync issue in the prior itunes version too. Although the Error 7 seems to relate to installing itunes 9.0.2.25 with Windows Server 2003 R2 I’m not so sure that the photo sync problem has anything to do with running on Server 2003..
Download Quicktime;
- Download iTunes64setup.exe, was not very easy, I used a file mirror website to find the link on Apple’s site;
- Download ORCA;
Done with downloads. Look -> nothing on my pockets nor my hands, now let’s do the magic:
- Install ORCA;
- Using Winrar (last version) or 7-Zip open and extract the files inside iTunes64setup.exe to a folder (ALL files, not only iTunes like I did at first try);
- Edit iTunes.msi with ORCA. I had a problem changing the launch condition, it wasn’t enough (I got an error when trying to install, error code 2229). To solve the problem I dropped the LauchnConditions table and in InstallExecuteSequence and InstallUISequence tables deleted the LaunchConditions action. After that save the MSI file and close ORCA;
Now to the easy part:
- Install AppleMobileDeviceSupport.msi;
- Install Quicktime you have downloaded;
- Install iTunes.
- Enjoy your nice product without buying a new Windows license
This install does not work on a new install of ITunes 9. However, I downloaded ITunes 8 and installed fine. I copied the v8 files to a temp folder. Then I checked for updates which downloaded the necessary files and the install failed. Then I installed the .msi files one at a time and saved the itunes.msi for last. When it failed due to the ipodservice error, I swapped back to the v8 files, selected “Retry” from the error message window and it worked fine.
Declare “Victory”
yes this method is working an i can connect my iphone to my server. the problem ist that almost every day itunes seams to detect the “manipulation” and replaces the files. any solution to this?
Probably too late for you to see this but I’m just wondering tenwiseman, did you actually test that method about changing the log on for the service? Only I tried doing the same thing, and changed the log on to my main admin account, but the service still kept crashing.
I think this method you mentioned seems like it would work at first glance, but doesn’t. The original assumption that iPodService.exe simply doesn’t work on Server 2003 is the correct assumption, because upon restarting the server I get various “iPodService.exe encountered a problem and had to be closed” notifications, and I’ve only ever got those when an exe actually caused an exception and crashed, and exe’s just don’t do that if the only problem they’re having is relating to permissions. I could be utterly wrong of course but I just thought I’d mention this in case anyone followed that advice and found it didn’t work – like me.
I have followed all the instructions for installing itunes v9 on windows 2003 but still get this message right at the end of the installer ”Service ‘Ipod service’ (ipod service) failed to start. Verify u have sufficient privilages to start system services!!’
I have regone through the ipod file with v8 & v9 instructions but am still having this problem!
Please help!!
Thanks