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Line a baking sheet with parchment paper and set aside.
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Combine cranberries and 1/4 cup of sugar in a food processor and process just until the cranberries are broken down into smaller pieces. Set aside.
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Combine flour and remaining sugar in a large bowl.
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Use a pastry cutter or two forks to cut in butter. You want very fine crumbs.
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Stir in extract, cranberries and sugar mixture, orange zest and orange juice (optional).
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Use your hands to knead the dough until it comes together and forms a ball. Work the dough until it comes together. If the dough is still crumbly, add orange juice, one tablespoon at a time until the dough comes together.
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Shape dough into a log about two inches in a diameter and wrap in plastic wrap. Refrigerate for two hours or up to 72 hours.
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Preheat oven to 325°F.
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Cut slices of cookie dough about ¼ inch thick.
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Place about a half a cup of sugar in a bowl and coat the cookie slices with sugar.
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Place cookies on baking sheet and bake for 12 to 15 minutes or just until cookies are set. Do not over bake. I remove my cookies at 12 minutes.
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Let cookies cool for several minutes on baking sheet before removing to cooling rack. Let cool completely.
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Store in airtight container for 3 days or freeze for up to 3 months.