iTunes LogoFor some reason, Apple has stopped supporting iTunes on Windows 2003 and changed their MSI installer to fail. However if you still prefer to run iTunes on your Windows 2003 Server, you can still modify the iTunes installer by using installer tools such as Microsoft Orca (see Microsoft’s Tutorial on how to modify MSI files) or InstEd. Using InstEd, I was able to install iTunes 9 on my Windows 2003 machine.

  1. First download the iTunes installer from
  2. Next use WinZip or WinRar to extract the contents of iTunesSetup.exe to a folder.
  3. Now comes the difficult part, you will need to check each of the .MSI files with InstEd or Orca. Open each file one at a time and look for the LaunchCondition settings. You will need to remove this parameter and its value: ((VersionNT=501 And ServicePackLevel>=2) OR VersionNT>501). Once you do that just Save and Exit.
  4. With the modified MSI files, now start installing them one at at time. Leave the iTunes.msi for last though. The SetupAdmin.exe can be ignored. You do not need to run that one.

If this was a perfect world, you would now be able to launch iTunes 9 on your machine, but since it is far from perfect, you might be staring at this error message:

The iPod Service service failed to start due to the following error: The service did not respond to the start or control request in a timely fashion.

To complete the install, leave the error up on the screen and go launch Services.msc, find the iPod Service and open its properties. You will need to add an account with admin rights and then save the changes. Now click Retry on the error and see if it works.

Additional Resources:


The easy fix that works, is to right click on the iTunes installer and choose Properties. Then go to the Compatibility tab and check “Run this program in compatibility mode for” and choose Windows XP from the pulldown list.