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Melt 1/4 cup butter in a saucepan over medium heat. Add the brown sugar, 1 1/2 tablespoons milk, and cook 2 minutes.
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Remove from the heat, and add vanilla and powdered sugar, and stir with a whisk until smooth. Spread this mixture evenly over the cooled brownies and let stand 20 minutes, or until set.
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Combine the remaining 2 tablespoons milk, and chocolate in a microwave-safe bowl, and microwave on high for 45 seconds, or until melted, stirring after 20 seconds. Stir just until smooth, and drizzle over the caramel.
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Sprinkle with sea salt, let stand until set, and cut into 20 squares.