In a food processor or a chopper, combine cranberries and 1/4 cup of sugar. Chop until the cranberries are in small pieces. You don’t need to pulverize it.
In a medium bowl, combine flour and 1/2 cup of sugar.
Use a pastry cutter or by using your fingers, cut in butter. You want very fine crumbs. About pea sized mixture.
Add in the cranberries and sugar mixture, vanilla extract orange zest and orange juice.
Use your hands to knead the dough until it comes together and forms a ball. Work the dough until it comes together. The dough will be moist.
Divide the dough into 2 balls. Shape the dough into a log about two inches in a diameter and wrap in plastic wrap. If you have an empty paper towel roll, put it inside the roll to keep its shape. Refrigerate for two hours or up to 72 hours.
Preheat oven to 325F. Line a baking sheet with parchment paper and set aside.
Cut slices of cookie dough about ΒΌ inch thick.
Place cookies on baking sheet and bake for 12 to 15 minutes or just until cookies are set. Check the cookies at the 12 minute mark to make sure that it’s not browning.
Let cookies cool for several minutes on baking sheet before removing to cooling rack. Let cool completely.