Pineapple Upside Sugar Cookies

 

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There’s something absolutely magical about the sweet tropical flavor of pineapple meeting the buttery charm of a soft sugar cookie. These Pineapple Upside Sugar Cookies take the beloved nostalgia of a classic pineapple upside-down cake and transform it into perfectly portioned, golden, chewy cookies with caramelized pineapple and a maraschino cherry center. Each bite bursts with sunny, tropical sweetness — the kind that makes you close your eyes and savor the moment.

These cookies are a showstopper for parties, bake sales, or summer gatherings, and they’re surprisingly simple to make. They bring together everything you love about pineapple upside-down cake — the gooey brown sugar topping, the tangy pineapple, the sweet cherries — in a portable, cookie-sized treat that’s both fun and elegant.

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🧁 Ingredients (and Why They Matter)

For the Topping:

½ cup brown sugar (light or dark) – Adds a deep, caramelized sweetness and gives the cookies that signature sticky, syrupy top.

4 tablespoons unsalted butter, melted – Helps the brown sugar melt and bubble as the cookies bake, creating that glossy upside-down finish.

12 pineapple rings (fresh or canned) – The star of the show! Sweet, tangy, and slightly tart, they balance the rich cookie base beautifully.

12 maraschino cherries – Add a pop of color and nostalgic flavor right in the center of each cookie.

For the Sugar Cookie Dough:

½ cup unsalted butter, softened – Creates a soft, rich, and buttery cookie texture.

¾ cup granulated sugar – Provides sweetness and helps achieve a delicate, chewy crumb.

1 large egg – Binds everything together and adds moisture.

1 teaspoon vanilla extract – Enhances flavor and gives the cookies a warm aroma.

1½ cups all-purpose flour – Forms the structure of the cookies while keeping them tender.

½ teaspoon baking powder – Helps the cookies puff up slightly for a soft, cakey texture.

¼ teaspoon salt – Balances sweetness and enhances the overall flavor profile.

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🍍 Step-by-Step Instructions

Step 1: Prepare the Topping

1. Preheat your oven to 350°F (175°C).

2. Lightly grease a muffin tin or line it with parchment rounds.

3. In a small bowl, mix together melted butter and brown sugar.

4. Spoon about 1 teaspoon of the mixture into the bottom of each muffin cup.

5. Place a pineapple ring on top of the brown sugar mixture and a maraschino cherry in the center of each ring.

Step 2: Make the Cookie Dough

1. In a large mixing bowl, cream together butter and sugar until light and fluffy.

2. Add the egg and vanilla extract, beating until fully combined.

3. In a separate bowl, whisk together flour, baking powder, and salt.

4. Gradually mix the dry ingredients into the wet ingredients until a soft dough forms.

Step 3: Assemble and Bake

1. Roll cookie dough into tablespoon-sized balls and flatten them slightly between your palms.

2. Place each dough round on top of a pineapple ring in the muffin tin.

3. Bake for 15–18 minutes, or until the cookies are golden and slightly firm on top.

4. Let them cool in the pan for about 5 minutes, then carefully invert onto a wire rack while still warm — revealing the beautiful caramelized pineapple and cherry top.

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🌟 Why You’ll Love This Recipe

Portable and Mess-Free – All the flavor of a cake in a hand-held cookie form.

Visually Stunning – Perfectly caramelized pineapple rings and bright red cherries make them irresistible.

Tropical Flavor Explosion – The tangy pineapple contrasts beautifully with the sweet, buttery cookie base.

Perfect Texture – Soft, chewy, and slightly crisp around the edges.

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💡 Pro Tips for Perfect Pineapple Upside Sugar Cookies

1. Use well-drained pineapple rings – Excess liquid can make the topping soggy.

2. Don’t overbake – The cookies should be just set; they’ll continue to firm up as they cool.

3. Cool slightly before flipping – Waiting 5 minutes helps the caramelized topping set slightly without sticking to the pan.

4. Add a hint of coconut extract to the dough for a tropical twist.

5. Serve warm – The gooey caramel and juicy pineapple are at their best when freshly baked.

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🍽️ Serving Suggestions

Serve these cookies warm with a scoop of vanilla ice cream for an instant dessert upgrade. They also pair beautifully with iced coffee, sweet tea, or a tropical fruit punch. For a festive touch, sprinkle with toasted coconut or a light dusting of powdered sugar before serving.

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✨ Final Thoughts

These Pineapple Upside Sugar Cookies are a creative, nostalgic twist on a classic dessert — bright, buttery, and irresistibly sweet. They’re as easy to make as they are impressive to serve, bringing sunshine to your dessert table any time of year.

Whether you’re baking for a summer cookout, a holiday gathering, or just a cozy weekend treat, these co

okies are guaranteed to make everyone smile. Simple, stunning, and packed with flavor — this is one recipe you’ll make again and again. 🍍💛