Despite the intricate design, these festive pinwheels are simple to create. The cream cheese in the cookie dough adds just the right amount of pliability, so you can cut, fold and shape with ease. We decorated the cookies with white, red and green coarse sanding sugar, sometimes called pearlized sugar, but you can feel free to swap in plain confectioners' sugar. They'll look stunning either way!
Beat the cream cheese, butter and granulated sugar in a large bowl with an electric mixer on medium-high speed until light and fluffy, about 2 minutes, scraping down the bowl with a rubber spatula as needed.
Reduce the mixer speed to low and beat in the flour and salt until combined. Divide the dough between 2 large pieces of plastic wrap. Flatten each into a 1/2-inch-thick disk and wrap. Refrigerate until firm, at least 1 hour and up to overnight.
Preheat the oven to 350 degrees F. Line 2 baking sheets with parchment.
Roll out 1 disk of dough on a lightly floured surface until about 1/8 inch thick, dusting with more flour as needed.
Cut out 3-inch squares using a sharp paring knife or a 3-inch square cutter (you should be able to get 6 or 7 squares). Lift the cutouts using an offset spatula and arrange 2 inches apart on one of the prepared baking sheets. Re-wrap and refrigerate the dough scraps while you shape the pinwheels.
Cut a 1 1/2-inch slit in all four corners of each dough square to form 8 points. Fold over every other point and press into the center of the square. Refrigerate while you make the leaves.
Cut enough leaves out of the scraps using a sharp paring knife or a leaf-shaped cutter, making 2 leaves for each pinwheel. Arrange the leaves on the other prepared baking sheet. Lightly brush with water and sprinkle with green sanding sugar. Set aside in the refrigerator.
Lightly brush the pinwheels with water and sprinkle half with red sanding sugar and half with white sanding sugar. Brush the end of 2 leaves and tuck underneath a pinwheel on opposite sides. (No need to press the dough; it will meld together as it bakes.)
Bake, rotating the baking sheet halfway through, until the cookies are puffed and the edges are golden, 20 to 25 minutes. Immediately press a chocolate candy in the center of each warm cookie. Let cool 5 minutes, then transfer the cookies to a wire rack to cool completely.
Repeat with the remaining disk of dough, and any remaining scraps, to make more cookies.
When measuring flour, we spoon it into a dry measuring cup and level off excess. (Scooping directly from the bag compacts the flour, resulting in dry baked goods.)
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