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Running a .exe

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Depends on the definition of "auto run". Not in the way that the autorun feature would work on old Windows versions. You could create a payload though that triggers an exe file. It has to be already present on the target, or downloaded from the internet/network since the classic generation 1 Ducky can't mount storage to the host (like the new Ducky can). It's possible, but you need alternative/unsupported third party firmware to make the classic Ducky act as a storage device.

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