Prep the oven and pan. Position a rack in the center of the oven and preheat it to 325°F. Line a baking sheet with parchment paper or lightly grease the pan.
Chop the cranberries. In a food processor, chopper, or by hand, chop the cranberries as finely as possible.
Make the cookie dough. Combine the flour with the chopped cranberries in a mixing bowl. Add the softened butter, confectioners’ sugar, and orange zest. Mix until a soft dough has formed.
Roll and cut out the cookies. Turn the dough out onto a lightly floured surface. Roll out the dough to a thickness of about 1/4 to 1/3 inch using a lightly floured rolling pin. Cut out with cookie cutters or cut into strips with a sharp knife.
Bake the cookies. Place them on the prepared baking sheet. Prick the cookies in a few places with a fork. Bake for 20 minutes or until just lightly browned on the bottoms.