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Line a baking sheet with parchment paper and set aside.
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In a large bowl, stir together the flour, sugar, baking powder, and salt. Using a pastry cutter or your hands, cut in the butter until the mixture has small, pea-sized chunks of shortening throughout.
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Stir in the buttermilk and vanilla until the dough begins to form. Turn the dough out onto a floured surface, and knead together gently until the dough comes together completely, being careful not to over-work it.
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Pat the dough into a rectangle about 7-8 inches long and 4 or so inches wide- it doesn't have to be perfect. Cut the dough into 6 even shortcakes, and place on your lined baking sheet. Put the whole thing into the freezer for 20 minutes.
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Meanwhile, preheat your oven to 400 degrees. Once the oven is preheated, pull the shortcakes out of the freezer. Brush the tops with remaining 2 tbs. buttermilk and sprinkle generously with the coarse sugar. Bake for 13-15 minutes, or until the tops are golden brown and the shortcakes have puffed.