There are 2 parts, firstly, how you automate the graphical interface, and secondly, how can I โcheckโ whether it works / does not work.
Firtsly: To automate the GUI on Windows, try using AutoIT. This is a free tool for managing Windows interfaces, sending keyboard input events, etc. http://www.autoitscript.com/autoit3/
Secondly: Testing is a big field, and I will not try to give you a whirlwind tour. But the mechanics of managing the graphical interface and testing the results can be processed using AutoIT, which is built into Basic as a language, or using it in combination with the Ruby language and TestUnit (Rubys built-in unit testing system).
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