Software Deployment

I have a native .MSI from a vendor. I created a .MST for this .MSI and inside of my .MST I call a Wise .EXE I wrote that does some stuff. It works fine when run manually.
Inside of the GPO management console I create a new GPO. Under "User Configuration\Policy\Software Settings" I call my MSI and MST. I also pick "run at logon" and make it Assigned.
Then, back in the GPO management console under the Security Filtering for this new GPO I add 4 workstations.
I then "Link" this GPO to a Computer OU

It never runs. I will run gpupdate /force on my 4 machines, reboot them etc....etc....and the policy never runs.

But......

If under the Security Filtering I remove the machines and add a User Account and then link this GPO to a User OU it Does work !! But then the MSI runs everytime the user logs in and we don't want that.

So I guess my question is can you have a User Configuration\Policy\Software Settings policy applied to a machine and make it only run at start up when the user logs in? And since it is assigned to the machine have it only run once.


What I am trying to install has to run under the Users context since it updates some data under the users profile.


Thank you.