I recently managed to cause myself a huge headache when removeing some software via group policy.
The worst part is, I only have myself to blame as the software was wrapped by me using Masai Installer.
If software uninstallation (or installation for that matter) goes bad, then a dialog window will open asking for some sort of input, which should never happen during silent installations.
If this happens while Windows is installing / uninstalling managed software, then Windows will hang and the only way to avoid the installation is to reset the computer.
The way around this is to make sure that you test the MSI by installing and then uninstalling.
The best way is to use these commands:
msiexec /i msifile.msi /qb
msiexec /x msifile.msi /qb
Of course, replace msifile.msi with the name of your MSI installer.
If the MSI installs and uninstalls without any prompts for input, then you know that it will deploy correctly through group policy.
If there is a prompt, then you need to work out how to prevent the prompt appearing during the installation.