Pineapple and coconut is one of my favorite flavor combinations, so for my favorite holiday, I combined the two into the perfect pina colada hamentaschen. The cookie is crispy and full of coconut flakes plus coconut extract for double the flavor. The homemade pineapple filling is so easy and delicious, you won’t believe it!
Makes 2 and 1/2 cups, and can be made a few days in advance and stored in the refrigerator.
In a medium pot, combine the canned pineapple (with its juice), sugar, cornstarch, and salt. Stir to make sure the sugar and cornstarch are combined.
Heat the mixture on medium heat for three to five minutes until thickened and clear; no longer cloudy. Make sure to stir frequently so the pineapple doesn’t burn.
Remove from heat, cover directly on the surface with plastic wrap so a skin does not form, and chill in the refrigerator until cool, at least 3 hours.
In the bowl of an electric stand mixer fitted with the paddle attachment, beat the shortening with the sugar and coconut extract until light and fluffy.
Add in the eggs and mix until combined.
Add in the flour, ground coconut, baking powder, and salt and slowly mix on low speed.
Pour in the pineapple juice and mix until a dough is formed. You can use the dough right away. If the dough is too sticky, wrap and chill in the refrigerator for a half hour.
On a lightly floured surface, or on a floured sheet of Gefen Parchment Paper, roll out a piece of the dough until thin.
Use a round cutter (two and a half to three inches) and cut out circles of dough.
Fill each round with a teaspoon of filling and pinch the edges together to form a triangle.
Transfer to parchment lined baking sheet and bake in a 350°F oven for 8–10 minutes until the edges begin to brown. Allow to cool and enjoy!