Microsoft offers a new tool that goes by the promising name Works With Tool for Windows Server 2008 (WWT). It allows you to test applications in order to see if they work properly under Windows Server 2008. Neil Hutson, a Microsoft evangelist, claims that you can "perform automated tests" with this free utility. I just played a little with the beta version today.
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WWT has an easy-to-use wizard that guides you thru the software evaluation process. It works a little like a software packager. WWT compares the system before and after the installation of the application. It will then give you information about the files installed such as their location, their version number, if they were signed, etc.
Next you have to check the functionality of your application. WWT will display a form where you have to answer several questions about the results of the test. For example, you have to tell WWT if the system and the application remained stable, if you experienced data loss and so on.
WWT can create an HTML report or you can store the results of your tests in a submission package which you could send to your software vendor. If they also use WWT they can examine the results of your test this way.
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I doubt that we will use WWT to test our applications. The tool certainly can't perform automated tests. If you really want to know if an application is working properly under Windows Server 2008, you have to check its functionality, manually. I wouldn't use software anyway on a new OS if this isn't supported officially by its vendor. And if you want to create a report of an evaluation process of a self-developed application, you usually have to add application specific data. WWT doesn't offer a way to include such information.