Hawaiian Dream Cookies

Total Time

Prep: 15 min. + chilling Bake: 15 min./batch + cooling


about 2 dozen

Updated: Oct. 15, 2022
These cookies are lovely as they are, but I'll sometimes use a light-colored sanding sugar for the top: First, lightly brush the top cookie with cream, then sprinkle with sanding sugar. This can be done before or after placing the cookie on top of the filling. —Lorraine Caland, Shuniah, Ontario
Hawaiian Dream Cookies Recipe photo by Taste of Home


  • 1/3 cup shortening
  • 1/3 cup butter, softened
  • 2/3 cup sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 1 teaspoon grated lemon zest
  • 2 cups all-purpose flour
  • 1-1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/4 cup sugar
  • 1 tablespoon cornstarch
  • 1 cup undrained crushed pineapple
  • 1/2 teaspoon butter
  • Confectioners' sugar


  1. In a large bowl, cream shortening, butter and sugar until light and fluffy. Beat in eggs, vanilla and lemon zest. In another bowl, whisk flour, baking powder and salt; gradually beat into creamed mixture. Divide dough in half. Shape each into a disk; wrap in plastic. Refrigerate 1 hour.
  2. Preheat oven to 350°. On a surface sprinkled with confectioners' sugar, roll dough to 1/4-in. thickness. Cut with a 2-in. round cookie cutter dusted with confectioners' sugar. Using a floured 1-in. star-shaped cookie cutter, cut out the centers of half of the cookies; re-roll scraps as needed. Place solid and window cookies 2 in. apart on greased baking sheets. Repeat with remaining dough.
  3. Bake 12-15 minutes or until edges are brown. Cool on pans 5 minutes. Remove to wire racks to cool completely.
  4. In a small saucepan, mix sugar and cornstarch. Stir in pineapple. Cook and stir over medium heat until thickened. Stir in butter. Cool completely. Spread filling on bottoms of solid cookies; top with window cookies. Dust with confectioners' sugar.

Nutrition Facts

1 cookie: 131 calories, 6g fat (2g saturated fat), 22mg cholesterol, 82mg sodium, 18g carbohydrate (10g sugars, 0 fiber), 2g protein.