Photo: Justin Walker; Styling: Missie Neville Crawford
Hands-on Time
1 Hour 13 Mins
Total Time
2 Hours 18 Mins
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.

How to Make It

Step 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).

Step 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.

Step 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°.

Step 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.

Ratings & Reviews

sprky182's Review

December 20, 2013
These came out nice. I was a little worried when the dough was hard to work with for the first few, but after it softened a little it became much easier. I recommend letting the dough soften before starting to avoid cracks and the pineapple coming through. I found rolling the dough slices into a long oval, adding 1 tsp of filling, and then folding each side over the middle and forming the dough into a flat circle to be the best way to keep the filling from leaking out. The flavor of the shortbread is very nice and it has a nice pineapple zing. They look like cute little knishes out of the oven, but a sprinkle of powdered sugar fixes that!


February 29, 2016
i found the dough difficult to work with, but once baked was nice and short with a good flavor and different look.  i think next time i will try a different method of construction, maybe more like a newton bar, may make things a little easier.  didn't care too much for the filling, so that may be changed as well.  

Athena53's Review

January 23, 2014
My first experience with shortbread! It didn't go very well, unfortunately. I under mixed the shortbread and then froze it(*face palm*), which made the dough very crumbly and hard to shape. Also, we were out of white sugar, and I subbed brown sugar for it in the filling. This made it taste and look like pineapple chutney( not an unpleasant taste, but a little different). Altogether very tasty.