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Pineapple Pockets

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A flattened cone of butter dough with a pineapple filling laced with the pleasant taste of caramel creates an unusually scrumptious cookie.

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Ingredients

  • DOUGH
  • 1 1/2 sticks unsalted butter, at room temperature
  • 1/4 cup granulated sugar
  • 1/2 cup powdered sugar
  • 1/8 teaspoon salt
  • 1 egg yolk
  • 1 teaspoon vanilla
  • 1 2/3 cups all-purpose flour
  • PINEAPPLE FILLING
  • 2 tablespoons water
  • 1/3 cup sugar
  • 1 8-ounce can crushed pineapple in unsweetened juice
  • 1/2 tablespoon unsalted butter

Details

Servings 4

Preparation

Step 1

1. Dough: In the large bowl of an electric mixer, cream the butter at medium-low speed until smooth, about 1 minute. Beat in the sugars and salt on medium speed until creamy. Add the egg yolk, then the vanilla, beating just until well combined and slightly fluffy, and scraping down the sides of the bowl. Lower the mixer speed, gradually add the flour, and mix until just thoroughly combined.

2. Divide the dough half and roll out one portion of dough at a time between 2 sheets of waxed paper to form a circle 11 inches in diameter and 1/8 inch thick. Leaving the dough circles between the sheets of waxed paper, transfer them to a baking sheet and refrigerate until firm, for at least 2 hours or up to 3 days; or freeze, well-wrapped, for up to a month.

3. Pineapple filling: In a 3-cup, heavy-bottomed saucepan, combine the sugar and water over low heat. Stir occasionally, washing down any sugar crystals clinging to the sides of the pan with a brush dipped in cold water, until the sugar is dissolved. Increase the heat to medium-high and cook, without stirring, until the sugar syrup becomes thicker and amber in color, about 8 minutes. Remove from the heat, and pour in the crushed pineapple with its juice all at once. Be careful, as the mixture will foam up. Stir the mixture with a wooden spoon to distribute the heat and blend the ingredients together. Return to the stove and cook over medium-high heat 4 minutes more, or until the mixture is golden and syrupy. Turn off the heat and stir in the butter. Pour the mixture into a small bowl and set aside until completely cool.

4. Adjust the rack to the lower third of the oven and preheat the oven to 325°F. Line 2 baking sheets with parchment paper.

5. Remove one dough circle package at a time from the refrigerator. Peel off the top sheet of waxed paper, replace it loosely on top, and flip the entire package over. Peel off and discard to second sheet of waxed paper.

6. Using a 2-inch round cutter, cut out circles in the dough. Place the circles on the baking sheets and spoon ½ teaspoon filling slightly off center on each. Fold over one edge of the dough, then overlap the opposite side to partially cover the filling. The cookie should look like a flattened cone with some filling showing at the wider end. Bake, one sheet at a time, for 12 to 14 minutes, or until the edges are light golden. Place the baking sheet on a wire rack to cool for 5 minutes. Then lift the cookies from parchment with a spatula to a rack to cool.

7. Stack cookies in an airtight container, separate the layers with strips of waxed paper to keep them from sticking together.

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