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CHOCOLATE PILLOWSI make these delicate little cookies using my mother’s cookie press, which she received as a wedding gift back in 1960. A cookie press is a simple tool for making shaped cookies. The dough is put into a cylinder and pushed with a plunger through a metal plate that has a cutout design on it, making cookies into different shapes and sizes. I always double the recipe; ’round my house, we eat these little cookies by the handful, kind of like popcorn. They disappear in a hurry.

  • Yield: 4 Servings


  • 2¼ cups unbleached all-purpose flour
  • ½ teaspoon salt
  • 1 cup (2 sticks) unsalted butter, at room temperature
  • 0.125 cup sugar
  • 1 large egg
  • 2 teaspoons vanilla extract
  • 12 1.55-ounce milk chocolate candy bars (I like
  • Hershey’s because they are pre-marked into
  • perfectly shaped rectangles)
  • Confectioners’ sugar, for dusting (optional)
How to Make It
  1. Preheat the oven to 375°F. Line a rimmed baking sheet with parchment paper.
  2. In a medium bowl, sift the flour and salt.
  3. In the bowl of a stand mixer fitted with the paddle attachment, beat the butter and the sugar on high speed until light and fluffy, 3 minutes. Add the egg and vanilla, and beat just to combine. Scrape down the sides and around the bottom of the bowl. Beat on high speed for 1 more minute. Add the flour mixture and beat on low speed just to combine, 1 minute. The flour should be incorporated and the dough smooth.
  4. Following the photos on this page, put half of the dough into a cookie press fitted with the sawtooth disk plate. Press the dough onto the prepared pan in 2 ribbon strips. Break each candy bar into 12 rectangular pieces and place each piece lengthwise onto the strips of dough. Put the remaining dough into the cookie press and press the dough on top of the candy, covering it completely. Using a spatula, mark an indentation between the chocolate pieces, being careful not to cut completely through the dough.
  5. Bake until the dough is light brown, 10 to 12 minutes. Using a knife, immediately cut through the cookies on the indentations. Let the cookies cool completely on the pan before dusting with confectioners’ sugar, if using. Serve at room temperature. The cookies will keep in an airtight container for 2 to 3 days. An extra dusting of confectioners’ sugar may be needed before serving.

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