If your application is an MSI (and it is setup correctly for silent installation) then you can easily roll it out as group policy fully supports MSIs. Here's the official guide from
Microsoft.
If your application is not an MSI then you have two options. You can either use a startup/logon script to install the software using the correct switches for silent installation or you can 'repackage' the application as an MSI and use the first step. I would recommend trying to get the application to install with its native installer first. Here's a
guide on setting up startup scripts and here's a
guide on the switches to use with different installers. If you a startup script to install the software (a batch file or a Visual Basic Script file) you’ll need some way to check if the program is already installed or it’ll install it every time you boot the computer up. You could try checking for the existence of a file (for instance the main exe) or a registry entry.
To repackage an application as an MSI you can use the Discover utility which is part of WinINSTALL LE 2003 which you can download
here. This version of the software is free, although it is no longer supported by the company. During the install you'll need to pull out the network cable when it tries to register as the registration server is no longer online. What it does is take a snapshot of your computer, then you install the software and then it compares the changes and produces an MSI. This method will work for troublesome installers although I would use it as a last resort as it can pick up changes that weren’t part of the installation and may not work for more complicated installations.
Well I hope that points you in the right direction. If you're having trouble with a popular piece of software try googling the problem as there will undoubtedly be thousands of network administrators out there who have tried the same thing.
Charlie