Cranberry Shortbread
['1 cup all-purpose flour', '3/4 cup sugar, divided', '1/4 teaspoon kosher salt', '1/2 cup (1 stick) chilled unsalted butter, cut into 1/2" cubes', '1 10-ounce bag fresh (or frozen, thawed) cranberries', '1/4 cup fresh grapefruit juice', '1 teaspoon grated grapefruit zest']
Preheat oven to 350°F. Line an 8x8x2" pan with parchment, leaving a 2" overhang on 2 opposite sides. Whisk flour, 1/4 cup sugar, and salt in a medium bowl. Using your fingertips, rub butter into dry ingredients until mixture resembles coarse meal.
Transfer to prepared pan; press evenly onto bottom of pan (using the bottom of a flat measuring cup works well). Prick dough all over with a fork.
Bake shortbread until cooked through and pale golden, 25-30 minutes. Transfer to a wire rack. Let cool completely in pan. DO AHEAD: Shortbread can be made 3 days ahead. Cover pan tightly with plastic wrap and store at room temperature.
Bring remaining 1/2 cup sugar, 1 1/2 cups cranberries, and grapefruit juice to a simmer in a small saucepan and cook, stirring occasionally, until cranberries burst and mixture is syrupy, about 8 minutes. Stir in remaining cranberries and cook until skins begin to split, about 3 minutes. Let cool. DO AHEAD: Cranberry topping can be made 3 days ahead. Cover and chill.
Spread cooled cranberry topping over shortbread. Scatter zest over. Using paper overhang, lift shortbread from pan and transfer to a cutting board. Cut shortbread.
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