Step 3: Arrange the Pineapple and Cherries
Place one pineapple slice on top of the caramel mixture in each cup. Press gently so it settles into the sugar. Add a cherry half in the center of each pineapple ring. This step gives the cookies their signature pineapple upside-down look.
Step 4: Make the Sugar Cookie Dough
In a large bowl, cream the softened butter and granulated sugar together until light and fluffy. Add the egg and vanilla extract, mixing until fully incorporated.
In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, mixing just until a soft dough forms. Avoid overmixing to keep the cookies tender.
Step 5: Assemble the Cookies
Scoop or flatten small portions of dough and gently place them over the pineapple slices. Carefully press the dough so it covers the fruit without pushing it out of place. The dough will spread slightly as it bakes.
Step 6: Bake to Perfection
Bake for 14–18 minutes, or until the cookie dough is lightly golden around the edges. The centers should be set but still soft.
Step 7: Flip and Reveal
Allow the cookies to cool in the pan for about 5 minutes. Then, carefully run a knife around the edges and invert the pan onto a baking sheet or cooling rack. Lift the pan slowly to reveal the glossy pineapple topping.
Step 8: Cool and Serve
Let the cookies cool completely before serving. As they cool, the caramel topping will set, giving the cookies a beautiful shine and rich flavor.
Tips for Best Results
- Drain pineapple slices thoroughly to avoid excess moisture.
- Use room-temperature butter for a smoother dough.
- Serve slightly warm for a gooey caramel texture, or chilled for a firmer bite.
Final Thoughts
Pineapple Upside Down Sugar Cookies are proof that classic desserts can be reinvented in fun and delicious ways. With their soft sugar cookie base, caramelized pineapple topping, and charming presentation, these cookies are guaranteed to impress. Whether for a family gathering or a sweet treat just because, this recipe brings tropical flavor and old-fashioned comfort together in every bite 🍍🍪
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