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
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