The latest versions of Windows Live Messenger consist of a very small initial installer, which performs checks on the system and determines whether the system meets requirements. Then, the installer downloads the full Windows Live Messenger installation MSI file and proceeds with the installation automatically.

The initial installer won’t install on Server 2008, even though Windows Live Messenger itself runs fine on Server 2008. To install it, you need to bypass the initial installer that performs the OS check and directly install the MSI file. There are numerous methods to obtain the Live Messenger installer. First, you can go to a site such as www.softpedia.com and search for Install_WLMessenger.msi or Windows Live Messenger. Second, on a Windows Vista machine, you can perform an installation of Windows Live Messenger, then go into Windows Explorer and remove the option to hide protected OS files. Browse to C:\Program Files\Common Files\WindowsLiveInstaller\MsiSources, and copy the MSI file to your Server 2008 machine. The latter is the safest option because you know the source of the files you’re using.