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To make the dough in a stand mixer, add the flour, sugar, salt, and butter to the bowl of your stand mixer fitted with the paddle attachment. Turn to low and mix for about 3 minutes or until the mixture is coarse crumbs with small chunks of butter throughout. Add the egg yolk and 3 tablespoons of milk and stir until just combined. You may need to add an additional tablespoon of milk to get the dough to come together.
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Remove the dough from the bowl, shape into a disk, and wrap in plastic wrap. Refrigerate for 30 minutes.
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To make the dough by hand, add the flour, sugar, salt, and butter to a large bowl. Use a pastry cutter or two butter knives to work the butter into the flour mixture. The flour should resemble coarse crumbs with small chunks of butter throughout. Use a wooden spoon to stir in the egg yolk and 3 tablespoons of milk. Mix just until the dough comes together. Use your hands to mix if needed. Add the additional tablespoon of milk if dough is too dry. Shape the dough into a disc, wrap in plastic wrap, and place in the fridge for 30 minutes.
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Roll the dough out on a lightly floured surface to a 1/4 inch thick. Take 8 wide mouth mason jar lids and place them on the dough. Use a knife to cut around them, leaving a 1/2 inch border around the lids. You will likely need to re-roll the dough to get all 8.
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Press the dough into the lids, crimp the edges, and prick all over with a fork.
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Refrigerate for 30 more minutes.
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Bake at 350 degrees for 18-20 minutes or until just beginning to turn golden. Cool completely before filling.
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To make the filling, heat the cream in a small saucepan over medium heat until it just begins to bubble. Place the chocolate chips in a medium bowl and pour the cream over the top. Whisk the mixture until melted and completely smooth. Pour about 2 tablespoons of the chocolate mixture into each shell.
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Top with as many raspberries as you'd like.
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Let cool to room temperature before refrigerating for 1 hour before serving.
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