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I've created a GPO to push out an .msi packages to PCs in a particular OU. I've confirmed that:

  • the target client PCs firewalls are not blocking traffic
  • the folder containing the .msi is shared on the network
  • the target PC's have had their GP updated via gpupdate /force

Is a log created which can help point me towards what the problem is? And secondarily, if the install push failed once, will it attempt to run again the next time the target PC's are rebooted?

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The client computer's Event Log wants to tell you what's wrong. Go look. –  Evan Anderson Feb 6 '12 at 17:51
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2 Answers

MSIs deployed via GPO will continue to attempt to reinstall. You need to verify that the share on the network is accessible via whatever account will be used to access the installation process. I have been bitten by this behavior in the past where the computer account was being used to run the installer but only domain users were granted access to the share.

If I remember correctly you should be able to use the MSI logging capacity to verify if the file is pulled down. If there is a failure pulling it down it should be reported in the clients system log.

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IF the MSI got launched at all that will show up in the Application Event log of the PC. As Tim Brigham mentioned security might be the culprit, to remove that as a factor, just ensure Authenticated Users have READ access at a minimum (this includes domain authenticated computers) - to the share and all subfolders and files.

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Nothing in the application log of the target PCs that relate to the msi install. I did just add authenticated users on the share, will test shortly. –  Citizen Chin Feb 6 '12 at 19:35
    
you'll also want to check to see if the GPO was applied to the computer at all. open CMD, run gpresult /r /scope computer and look at the Applied Group Policy Objects section to confirm the GPO was applied. –  Jordan W. Feb 7 '12 at 21:04
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