Convert .exe installer to msi, to be able to deploy through GPO

I'm no expert on GPO software deployment. However the damn system has given me so many problems in the past I've done a bit of reading and I'll summarize my opinion. I wouldn't call it fact unless you can find technical documents to prove/disprove it.

• When you deploy an MSI via Group Policy, it's up to the MSI to detect and uninstall or upgrade old/incompatible versions. This is a function of the msi and Microsoft Installer.

  Adobe are pretty good in this regard and appear to fully program their MSIs for upgrades where appropriate.

  (I have my suspicions that upgrades that need to reboot after the uninstall before installing the new version fail over Group Policy, because of below, but this is untested.)

• I'm pretty sure the MSI never makes it onto the local computer. The machine account runs it from the shared location (UNC) you provided it in the GPO.

• It depends on the software install settings in the GPO, but when your client boots, it runs through the machine GPOs, detects the software GPO, has a log that it's already processed it, so it moves on to the next GPO.

  This may cause installers that have to run twice (ie uninstall the old version, reboot, then install the new version) to fail. I developed this opinion because when I deployed Acrobat on a range of desktops, one of them uninstalled the old version but the GPO never installed the new version, I did this manually.

• There are settings in the GPO to remove the software if it's no longer linked etc, and obviously if these conditions change some re-processing (ie uninstall) would occur.

Diagnosing 'silent' MSI installation failures can be done like this:

Firstly, check your GPO is applying correctly. Use the Group Policy Management Console to run a report on a target machine, and view this report to check that the GPO that assigns the software installation is applying correctly. If this part isn't working right then there's no point in going any further. Both a fault in the GPO in question or in any other GPO that should be applied before or alongside it can cause a workstation to stop processing GPOs.

With that done, check the event logs on the target machine:

Open Computer management -> event viewer -> Windows Logs - Application

You're looking for errors with a source of MsiInstaller (and any other events that get logged at the same time of course).

Finally, a lot of applications record their own log as part of the installation process. If you can find the local folder that the MSI installation was ran from then there may be a detailed error log inside that (of course, if you can find errors in the windows event viewer then this will hopefully also mention the application logfile and tell you where to find it)

Also check that the following setting is being applied to the target computers via GPO, and if not, set it and then run gpupdate /force from a command line on a target computer, and reboot.

Computer Settings

  -> Administrative Templates
    -> System
      -> Logon
        -> Always wait for the network at computer startup and logon – Enabled