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Prepare Shortbread recipe through step 1, form into a disk, and chill 30 minutes.
On a lightly floured work surface, roll dough 1/8 in. thick. Use a selection of 1½-in. decorative cutters to cut as many shapes as you can, making sure you have an equal number of each shape to form a top and a bottom, and rerolling scraps as needed.
Arrange cookies 1 in. apart on baking sheets. Use a variety of smaller cutters to remove center from half of cookies (the tops). Chill on sheets 15 minutes; then bake until light golden brown, 12 to 15 minutes. Let cool.
Spread each whole cookie with about 1/2 tsp. raspberry preserves. Sprinkle powdered sugar over cut-out cookie tops, or glaze them with a mixture of 1 cup powdered sugar and 21/2 tsp. milk. Set tops on jam-topped bottoms. Makes 26.