A Classic Dessert Reimagined in Cookie Form
Introduction
Pineapple Upside Down Sugar Cookies take everything we love about the nostalgic pineapple upside-down cake—caramelized fruit, buttery sweetness, and eye-catching presentation—and transform it into a soft, handheld treat. These tender, golden cookies are topped with glossy pineapple slices and bright maraschino cherries, making them ideal for parties, holidays, or anytime you want a dessert that’s as beautiful as it is delicious.
Unlike traditional cookies, these are baked upside down, allowing the pineapple and caramel topping to become the star once flipped. The result is a bakery-style cookie with a tropical twist and irresistible flavor.
Ingredients You’ll Need
For the Topping:
- Pineapple slices (canned rings, well drained)
- Maraschino cherries, halved
- Unsalted butter, melted
- Brown sugar
For the Sugar Cookie Dough:
- Unsalted butter, softened
- Granulated sugar
- 1 large egg
- Vanilla extract
- All-purpose flour
- Baking powder
- Salt
Step-by-Step Method
Step 1: Prepare the Baking Pan
Preheat the oven to 350°F (175°C). Lightly grease a muffin tin or line it with parchment circles to prevent sticking. A muffin tin works best for holding the pineapple slices in place and giving each cookie a neat, uniform shape.
Step 2: Create the Caramel Base
In a small bowl, mix the melted butter and brown sugar until smooth. Spoon a small amount of this mixture into the bottom of each muffin cup, spreading it evenly. As the cookies bake, this layer melts into a rich, golden caramel.
Step 3: Arrange the Pineapple and Cherries
Place one pineapple slice on top of the caramel mixture in each cup, pressing gently so it settles. Add a cherry half in the center of each pineapple ring for that classic upside-down cake 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 shifting it. The dough will spread slightly during baking.
Step 6: Bake to Perfection
Bake for 14–18 minutes, or until the edges are lightly golden and the centers are set but still soft.
Step 7: Flip and Reveal
Let the cookies cool in the pan for about 5 minutes. Run a knife gently around the edges, then invert the pan onto a baking sheet or cooling rack. Lift slowly to reveal the glossy pineapple topping.
Step 8: Cool and Serve
Allow the cookies to 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 prevent excess moisture.
- Use room-temperature butter for smoother dough and even baking.
- Serve slightly warm for a gooey caramel texture or chilled for a firmer bite.
Final Thoughts
Pineapple Upside Down Sugar Cookies prove that classic desserts can be reinvented in fun, irresistible ways. With a soft sugar cookie base, caramelized pineapple topping, and charming presentation, these cookies are guaranteed to impress. Perfect for gatherings or a sweet treat “just because,” they bring tropical flavor and old-fashioned comfort together in every bite.
