Shortbread can be made up 2 days ahead of time. Cover and store at room temperature. Cranberry topping can be made 3 days prior. Cover and store in the refrigerator.
Preheat oven to 350 degrees. Line an 8x8x2 pan with parchment paper, leaving an overhang on 2 of the sides (for easy removal from pan after baking).
Whisk flour, 1/4 cup sugar, and salt in a medium bowl. Using your fingers, rub the butter into the dry ingredients, making a course meal. You can also use a pastry blender.
Transfer the mixture to the prepared pan, pressing the dough firmly onto the bottom of the pan.
Bake shortbread until cooked through and golden, about 30 minutes. Transfer to a wire rack to cool.
Bring the cranberries, 1/2 cup sugar, and fresh orange juice to a simmer in a saucepan and cook for about 8-10 minutes. Let the mixture cool.
Mix the sour cream, honey, and Grand Marnier together in a small bowl.
Using paper overhang, lift the shortbread from the pan and transfer to a cutting board or a serving platter.
On the cooled shortbread, spread the sour cream mixture. Top with the cooled cranberry mixture, spreading evenly on the crust.
Zest 2 tsp. of orange rind and sprinkle on top. Cut into 16 pieces and serve.