If you love the tropical sweetness of pineapple and the comforting nostalgia of soft sugar cookies, this Pineapple Upside Down Sugar Cookies Recipe will become your new favorite dessert. Imagine buttery golden cookies topped with caramelized pineapple and a juicy maraschino cherry—just like the classic cake, but in perfectly portioned handheld form. These cookies are fun, eye-catching, and absolutely irresistible, making them ideal for parties, holidays, or whenever you want a treat that stands out.
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Why You’ll Love These Pineapple Upside Down Sugar Cookies
These cookies combine the buttery softness of sugar cookies with the sweet, caramelized topping of pineapple upside down cake. They’re both chewy and juicy, with every bite delivering the tropical flavors of pineapple, cherry, and caramelized brown sugar. Unlike cake, they’re easy to serve, mess-free, and look gorgeous right off the baking sheet.
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Ingredients (and Why They Work)
For the Topping:
2 tablespoons unsalted butter (melted): Creates the rich caramel base for the pineapple.
½ cup brown sugar: Caramelizes beautifully and balances the tart pineapple.
12 pineapple rings (canned, drained): The star ingredient, bringing juicy tropical flavor.
12 maraschino cherries: A sweet, colorful touch in the center of each pineapple ring.
For the Cookie Dough:
½ cup unsalted butter (softened): The foundation of the cookie, providing richness and tenderness.
½ cup granulated sugar: Sweetens and helps create that classic sugar cookie texture.
½ cup brown sugar: Adds depth and a hint of molasses flavor.
1 large egg: Binds the dough together and ensures the cookies bake up soft.
1 teaspoon vanilla extract: Enhances the cookie’s flavor profile with warm sweetness.
1 ½ cups all-purpose flour: The base structure of the dough, ensuring the cookies hold their shape.
½ teaspoon baking powder: Provides a slight lift and softness.
¼ teaspoon salt: Balances sweetness and deepens flavor.
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Step-by-Step Instructions
Step 1: Prepare the Topping
1. Preheat oven to 350°F (175°C) and lightly grease a muffin pan.
2. In each muffin cup, add ½ teaspoon melted butter and sprinkle with 1 teaspoon brown sugar.
3. Place one pineapple ring in each cup. If needed, trim the pineapple to fit.
4. Add a maraschino cherry in the center of each ring.
Step 2: Make the Cookie Dough
1. In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy.
2. Beat in the egg and vanilla extract until smooth.
3. In a separate bowl, whisk together flour, baking powder, and salt.
4. Gradually mix the dry ingredients into the wet until a soft dough forms.
Step 3: Assemble and Bake
1. Scoop about 2 tablespoons of cookie dough and gently press it over the pineapple in each muffin cup.
2. Bake for 18–22 minutes, or until the cookies are golden and set.
3. Allow to cool for 5 minutes, then carefully invert the pan onto a baking sheet or platter to release the cookies.
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Pro Tips for Perfect Pineapple Upside Down Cookies
Drain the pineapple well: Too much juice will make the topping soggy. Pat dry with paper towels.
Don’t skip the brown sugar: It caramelizes into a glossy glaze that makes these cookies irresistible.
Use a muffin pan: It helps the cookies keep their shape and holds the topping in place.
Invert while warm: The topping releases more easily before the caramel sets too hard.
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Serving Suggestions
These cookies are fantastic on their own, but you can elevate them by serving with:
A scoop of vanilla ice cream for a pineapple sundae twist.
A dollop of whipped cream for added lightness.
A sprinkle of toasted coconut for an extra tropical flair.
They pair perfectly with iced tea, piña coladas, or a simple cup of coffee.
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Why This Recipe is Loved
Portable and shareable: All the flavor of pineapple upside down cake in a cookie form.
Visually stunning: The glossy pineapple and bright cherry make them party-ready.
Easy to make: Simple ingredients, straightforward steps, and guaranteed crowd-pleasing results.
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Final Thoughts
These Pineapple Upside Down Sugar Cookies prove that a classic cake can be reimagined into a fun, handheld treat without losing its charm. They’re easy, flavorful,
and beautiful—perfect for any occasion. With their buttery cookie base and sweet pineapple topping, they’re guaranteed to disappear quickly.
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