Taiwanese Pineapple Cakes

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1. 1Step 1: In a medium saucepan, combine the pineapple, granulated sugar, salt, and vanilla extract. Cook over medium heat, stirring frequently, until thick and caramelized, 20 to 30 minutes. Transfer the filling to a heat-proof container and allow to cool completely at room temperature (or refrigerate until ready to form the cakes).
2. 2Step 2: In the bowl of a food processor, pulse to combine the flour, confectioners' sugar, tapioca starch, salt, butter, and egg until a cohesive dough forms.
3. 3Step 3: Transfer the dough to a sheet of plastic wrap, pat into a 1-inch-thick disc, and tightly wrap. Refrigerate the dough until firm but still somewhat pliable, 30 to 45 minutes.
4. 4Step 4: Preheat the oven to 350°F and line a large rimmed baking sheet with parchment paper.
5. 5Step 5: Use a bench scraper to divide the dough into 18 equal-size pieces (use a digital scale if you have one). Working with one piece at a time, roll the dough into a smooth ball. Place the dough ball on a lightly floured work surface, gently flatten with the palm of your hand, and roll out to a 3-inch round with a dowel rolling pin. Place a teaspoon filling in the center of the dough, pull up the edges, and pinch together to seal. Place the filled cake inside the pineapple cake mold, seam side down, and gently press down with the plunger until it evenly fills the mold. Remove the plunger and transfer the pineapple cake, still in the mold, onto the prepared baking sheet. Repeat with the remaining pastry and pineapple filling. If you have a limited number of molds, keep the dough and filling in the refrigerator until ready to form the next batch.
6. 6Step 6: Bake in the molds until the cakes are golden brown, 25 to 27 minutes. Transfer the sheet to a wire rack and allow the cakes to cool on the sheet for 5 minutes. Remove the molds and allow the cakes to cool completely on the rack. Enjoy the cakes fresh or store in an airtight container for 24 hours to allow the shortbread to soften.