Combine cranberries and 1/4 cup of sugar into a food processor and process into smaller pieces. Set aside.
Combine flour and remaining sugar in a large bowl.
Using a pastry cutter, cut butter into flour mixture until you have fine crumbs.
Stir in vanilla, cranberries and sugar mixture, orange zest from an orange, and the 2 TBS of orange juice squeezed from same orange.
Using your hands, knead the dough until it comes together and forms a ball.
Shape dough into a log about 2 inches in diameter and wrap in plastic wrap. Refrigerate for two hours or up to 72 hours.
preheat oven to 325 degrees.
Cut cookie dough into 1/4 inch slices. Place 1/2 cup of sugar onto a plate and coat the cookie slices on both sides.
Place cookies on a lined baking sheet. Bake for 12-15 minutes until cookies are set.
Let cookies cool for several minutes on baking sheet, then remove to cooking rack. Let cool completely.
Enjoy.
