Install msi using group policy

You're seeing the dreaded scourge of asynchronous policy processing. It's not a "feature" (and was default-off in Windows 2000 but default-on in Windows XP and above) and causes exactly what you're seeing-- non-deterministic behaviour with processing some types of GPO settings.

In a GPO that applies to that computer, add the following setting:

• Computer Settings
  • Administrative Templates
    • System
      • Logon
        • Always wait for the network at computer startup and logon - Enabled

After you set that (and allow the GPO to replicate if you're in a multi-DC environment), do a "gpupdate /force /boot" on the subject PC. It will reboot and you should see the software installation occur.

The "Always wait for the network at computer startup and logon" slightly slows down the startup and logon because all GPO extensions are allowed to process, but the upside is that all GPO extensions are allowed to process.

That's bad mojo, then. That's nothing that you're doing w/ your procedure, but rather something wrong with the MSI. Did you build the MSI yourself or is it 3rd party? If it's third party, does the manufacturer indicate the MSI works in this type of deployment scenario?

I can't tell you which specific validations you should run because I don't know exactly what Windows is doing when it "extracts" the "deployment information" out of the MSI. I know that I've seen this with a couple of fairly poorly made MSIs from third parties. I belive that I ended up giving up on them, extracting the contents myself, and re-packaging them into MSIs w/ WiX.

(This is one of those places in Windows where I'd love to have some visibility into the source code...)