Rules FAQ
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If the location that was targeted by assault is already kneeling when you win the challenge, it will not be knelt by assault, so you cannot trigger Deepwood Motte.
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The location is knelt before reactions to winning the challenge can be initiated, so the reaction of Deepwood Motte always comes first. Once you move onto reactions to winning the challenge, you can no longer trigger Deepwood Motte. In other words, if you bring Deepwood Motte into play with something like Support of the People, the reaction window for its ability will have already closed.