Preheat oven to 375°F. Mix brown sugar, vanilla extract, salt, melted butter, and flour for shortbread. Press into a baking vessel, dock with a fork, and bake for 15-20 minutes.
Prepare caramel by combining butter, sweetened condensed milk, brown sugar, corn syrup, cream, and salt. Cook until 236°F, then pour over cooled shortbread.
Melt 6 oz of dark chocolate, then stir in remaining 2 oz until it reaches 82°F. Pour over caramel layer and refrigerate until set. Slice into bars and serve.
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