1cup225g / 2 sticks unsalted butter, room temperature
½cup60g confectioners' sugar, sifted
2large egg yolksroom temperature
1teaspoonvanilla extract
1¾cups220g cake flour, sifted
3tablespoonsfull-fat milk powder
¼teaspoonsalt
Instructions
Make the pineapple jam:
Peel and grate the fresh pineapple on the coarse side of a box grater. Include the core. You should have about 3 cups with juice.
Place the grated pineapple and all its juice into a wide non-stick skillet over medium-high heat. Cook, stirring occasionally, for 20–25 minutes until most moisture has evaporated.
Reduce to low heat. Add sugar, butter, and lemon juice. Stir constantly for 5–8 minutes until the jam is thick and holds a trail when you drag a spoon through it. Color will deepen to amber-gold.
Spread on a plate to cool completely — at least 30 minutes, or refrigerate for 20 minutes to speed up.
Make the shortbread crust:
Beat room-temperature butter and confectioners' sugar on medium speed for 3–4 minutes until pale and fluffy.
Add egg yolks one at a time, beating well after each.
Add vanilla extract and mix.
Sift in cake flour, milk powder, and salt. Fold in by hand with a spatula until just combined. Do not overmix.
If dough is sticky, refrigerate for 20 minutes.
Assemble and bake:
Preheat oven to 325°F (165°C). Line a baking pan with parchment.
Portion 30g dough and 15g jam for each cake (or 1 heaping tablespoon dough + 1 teaspoon jam).
Flatten the dough in your palm into a 3-inch disc. Place jam in the center. Bring dough up around the filling and pinch firmly to seal. Roll smooth.
Place in the lined pan. Press each into a square shape using the flat bottom of a small glass.
Refrigerate shaped cakes for 15–20 minutes before baking.
Bake 10–11 minutes. Flip each cake with a thin spatula. Bake another 10–11 minutes until pale golden-brown.
Cool in pan for 15 minutes. Transfer to wire rack and cool completely — minimum 1 hour before eating.
Notes
These taste best on day 2. Make them ahead whenever possible.
Dough cracking = dough is too cold or no egg yolks. Fix: warm to room temperature and add an extra yolk if needed.
Runny jam = needs more cooking time. Return to pan over low heat and cook until it holds a trail.