Specify original msi install location for msp file using a command line switch

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.

You can't do this with a single program unfortunately. BUT, you can do this with a single package (group of files, the msi in your case) using multiple programs. Using this approach you wouldn't have to update your programs whenever you update the package. The package is just the group of files (in most cases), the programs are the commands that are actually executed. In your situation, I would go with this approach:

1)You can create two separate install programs, and advertise them to the two different collections. Remember, these are not separate packages, but programs within a single package. The only time you would need to change the programs (which in practice is quite trivial) is when the command to install the package has changed. So if package A is script.msi I would create two programs for that package,

Program 1 whose command is msiexec /i script.msi /qb ALLUSERS=1

Program 2 whose command is msiexec /i script.msi

I would then deploy the two programs to their respective collections. If package A ever has to be updated to a new version of script.msi, I would just make sure to keep the name the same, and then update the distribution point with the latest version. You could of course send out a new required deployment to make sure clients have the latest version, but there is no need for two separate packages.