Combine cranberries and 1/4 cup of sugar in a food processor and process just until the cranberries are broken down into smaller pieces. Pour into a bowl and set aside.
Combine flour, salt and remaining sugar into the food processor. Add the cubed butter and pulse until you have very fine crumbs.
Pour flour mixture into a large mixing bowl and combine with cranberry and sugar mixture. Stir in 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.
Shape dough into a log by rolling it out until it's about two inches in diameter. Cover with plastic wrap. Refrigerate for two hours or up to 72 hours.
Preheat oven to 325F.
Line a baking sheet with parchment paper and set aside.
Using a large sharp knife, cut slices of cookie dough about ¼ inch thick.
Place about a half a cup of sugar in a bowl and coat the cookie slices with sugar.
Place cookies on baking sheet and bake for 12 to 15 minutes or just until cookies are set. Do not over bake. In my oven, they need the full 15 minutes but if you're using a fan oven pull them at 12. You may need to experiment with the time to find what works for your oven.
Let cookies cool for 15 minutes on baking sheet before removing to cooling rack. Let cool completely.
Store in airtight container for 3 days or freeze for up to 3 months.