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Comment on Ask HN: Is there any good OSS for interactive Windows automation?

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Well this might not meet your needs (and it has been a lot of years since I've used it because I don't do Windows anymore) but I believe Wix wixtoolset.org is still the default way of building installers for Windows.

When I used it I built a tool to generate installers for an enterprise product so that the consultants who were going out to the government organization to install the product could have a premade installer that did 80% of the work for them when they got there.

Perhaps you could build what you need if you find a sample installer that meets your needs, some good examples here https://github.com/rstropek/Samples/tree/master/WiXSamples

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