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Test stand in the cloud with the installation of proprietary software with a GUI, where to dig?
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So you formulate the question, what exactly does not work.
If the question is about automatic installation of an application - well, any application is ultimately just files and maybe a little bit of the registry.
You can take a clean virtual machine, turn on regmon / filemon and track what and where the installer puts. Then it will be possible to install it manually without the installer.
Of course, docker for Windows applications is possible, but docker is still more designed for the Linux area. In the case of the cloud, it is easier to make an image for a virtual machine from which to clone and run a test machine. But it depends on what you need.
But first of all, still more specifically formulate what you want
Start with an "algorithm" for manually installing and running tests, and then think about how to automate each step. The algorithm is usually divided into two parts: a one-time installation (you can do it manually and prepare an image of the machine), and what we do at each start.
I use Jenkins as my orchestration tool.
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