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How to test a Windows application on multiple OS versions

.NET is an abstraction layer between OS and your application. You should not be too worried about how its working on different version of Windows.

If you have some IO related functionality in your software, its smart to install software under users own folder to minimize risks of security issues. Also use only files under applications installation root folder.

In my experience companies usually have few virtual machines for major OS versions and they basically execute manual testing for critical functionality.

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