Preheat to 350°F (175°C) and line a baking sheet with parchment paper.
Prepare cookie dough:
In a large bowl, cream together butter and sugar until light and fluffy.
Beat in the egg and vanilla extract.
In a separate bowl, whisk together flour, baking powder, and salt. Gradually mix into the wet ingredients until a soft dough forms.
Prepare pineapple topping:
In a small bowl, combine crushed pineapple, brown sugar, and melted butter. Mix well.
Assemble cookies:
Scoop about 1–2 tablespoons of cookie dough and flatten slightly in your hand.
Press a small amount (about 1 teaspoon) of the pineapple mixture into the center and fold dough around it, sealing the pineapple inside.
Place on the prepared baking sheet about 2 inches apart.
Bake:
Bake for 12–15 minutes, or until the edges are lightly golden.
Remove from oven and let cookies cool slightly on the pan before transferring to a wire rack.
Serve:
Enjoy warm or at room temperature. These cookies have a soft, tropical center with a sweet, buttery exterior.
Tips:
Make sure the pineapple is well-drained to prevent the cookies from being too wet.
For extra flavor, sprinkle a pinch of cinnamon or nutmeg into the pineapple mixture.
These cookies can also be lightly glazed with powdered sugar and milk for a sweet finish.
If you want, I can also give you a single-layer pineapple upside-down cookie bar version—easier to make and perfect for sharing. Do you want me to do that?
