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Pineapple Shortbread Cakes

Photo: Justin Walker; Styling: Missie Neville Crawford
Hands-on time 1 hr, 13 mins
Total time 2 hrs, 18 mins
Yield Serves 24 (serving size: 1 cake)
Deliver Pineapple Shortbread Cakes for special indulgences for those special friends. These delicious, buttery cakes are a labor of love but absolutely worth the time you'll spend making them.


  • Filling:
  • 3 (8-ounce) cans crushed pineapple in juice, undrained
  • 3/4 cup granulated sugar
  • 1/4 teaspoon salt
  • 1/3 cup light-colored corn syrup
  • 4 teaspoons all-purpose flour
  • Shortbread:
  • 1/3 cup nonfat dry milk
  • 9 ounces cake flour (about 2 1/4 cups)
  • 1/4 teaspoon salt
  • 1/4 teaspoon baking powder
  • 12 tablespoons unsalted butter, softened
  • 1/2 cup powdered sugar
  • 2 large egg yolks
  • 1 tablespoon powdered sugar (optional)

Nutrition Information

  • calories 158
  • fat 6.3 g
  • satfat 3.8 g
  • monofat 1.7 g
  • polyfat 0.3 g
  • protein 1.6 g
  • carbohydrate 24.7 g
  • fiber 0.4 g
  • cholesterol 31 mg
  • iron 0.9 mg
  • sodium 64 mg
  • calcium 23 mg

How to Make It

  1. To prepare filling, drain pineapple in a fine-mesh sieve, pressing solids; reserve juice for another use. Place pineapple in a medium saucepan over medium-low heat; cook 15 minutes or until liquid evaporates, stirring frequently. Add granulated sugar and 1/4 teaspoon salt; cook 10 minutes or until liquid mostly evaporates, stirring occasionally. Add corn syrup; cook 5 minutes or until mixture is thick and sticky, stirring frequently. Add all-purpose flour; cook 1 minute or until very thick, stirring constantly. Scrape mixture onto a baking sheet, and spread into a thin layer; cover and chill completely (about 20 minutes).

  2. To prepare shortbread, sift dry milk into a bowl. Weigh or lightly spoon cake flour into dry measuring cups; level with a knife. Sift together dry milk, cake flour, 1/4 teaspoon salt, and baking powder. Place butter in a large bowl; beat with a mixer at medium speed until smooth and creamy. Add 1/2 cup powdered sugar; beat 2 minutes or until well combined. Add egg yolks, 1 at a time, beating well after each addition. Beat 2 minutes or until fluffy. Add flour mixture; beat at low speed just until combined. Divide dough in half. Gently shape dough into 2 (10-inch) logs; cover with plastic wrap. Chill 30 minutes.

  3. Arrange 1 oven rack 2 positions down from the top of oven; arrange another rack 2 positions up from bottom of oven. Preheat oven to 325°.

  4. Cut each dough log into 12 equal pieces. Working with 1 piece at a time, roll dough into a 3-inch circle on a lightly floured surface. Place about 1 tablespoon filling in the center; bring edges together over filling, and pinch closed. Gently press into a floured 1 3/4-inch square mold or cookie cutter, or shape into a square shape by hand. Place cake on a parchment-lined baking sheet. Repeat procedure with remaining dough and filling, placing cakes 2 inches apart on 2 parchment-lined baking sheets (12 cakes per sheet). Bake at 325° for 25 minutes, turning cakes over and rotating pans after 15 minutes. Remove cakes from pans, and cool completely on wire racks. Sprinkle with 1 tablespoon powdered sugar, if desired.