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opencv even has `message(WARNING "The python module is currently unsupported on Windows when building static OpenCV libraries")` In general static python builds don't support extensions on windows as such a pyd build against a static python can never be used. What would work -> static extensions linked into a final executable. There is no proper way to deactivate extensions if python was statically build on windows. Two questions remain here: Should python be build dynamically on windows for static triplets so that we get a broader CI test? (maybe add a forbidden feature for only windows&static which allows building the static python instead)