Hey y'all! If you love the classic flavors of pineapple upside-down cake but want a fun, bite-sized treat, these Pineapple Upside-Down Sugar Cookies are about to become your new favorite dessert. They’re buttery, soft, and bursting with caramelized pineapple goodness, making them perfect for parties, picnics, or just a sweet weeknight treat. Ready to impress your friends and family with a tropical twist? Let's get cooking!
Why You'll Love This Pineapple Upside-Down Sugar Cookies Recipe
- Combines the nostalgic taste of pineapple upside-down cake with the convenience of cookies.
- Perfectly portioned for easy serving at gatherings or as lunchbox treats.
- Quick to make—no need for fancy techniques or ingredients!
- Delivers a delightful mix of gooey, caramelized fruit and soft, chewy sugar cookie texture.
- Easy to customize with different fruits or flavor add-ins.
Ingredients for Pineapple Upside-Down Sugar Cookies
- 1 cup (200g) granulated sugar
- ½ cup (115g) unsalted butter, softened
- 1 large egg
- 1 teaspoon vanilla extract
- 1 ¾ cups (220g) all-purpose flour
- ½ teaspoon baking powder
- ¼ teaspoon baking soda
- ¼ teaspoon salt
- ¼ cup (55g) light brown sugar
- 6-8 maraschino cherries, halved
- 1 can (8 oz) pineapple rings or tidbits, drained and patted dry
- Optional: 1 tablespoon pineapple juice (from the can)
How to Make Pineapple Upside-Down Sugar Cookies
Step 1: Prepare the Topping
Preheat your oven to 350°F (175°C) and lightly grease a standard muffin tin. Sprinkle about 1 teaspoon of brown sugar into the bottom of each cup. Place a piece of pineapple (half a ring or a few tidbits) and half a maraschino cherry on top of the brown sugar layer in each cup.
Step 2: Make the Sugar Cookie Dough
In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy (about 2-3 minutes). Beat in the egg and vanilla extract until combined.
Step 3: Combine Dry Ingredients
In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually add to the wet ingredients, mixing until a soft dough forms. If the dough seems dry, mix in 1 tablespoon of reserved pineapple juice for extra flavor and moisture.
Step 4: Assemble the Cookies
Scoop about 2 tablespoons of dough and flatten slightly. Place each piece of dough over the pineapple and cherry in each muffin cup, pressing gently to cover the fruit and brown sugar.
Step 5: Bake the Cookies
Bake in the preheated oven for 12-14 minutes, or until the cookie tops are just set and lightly golden. Let cool in the pan for 5 minutes, then carefully invert onto a wire rack to cool completely, allowing the gooey, caramelized pineapple topping to shine.
Notes for Perfect Pineapple Upside-Down Sugar Cookies
- Pat the pineapple very dry to avoid soggy cookies and ensure caramelization.
- Don’t skip inverting the cookies while they're still warm to prevent sticking; check these tips for non-stick baking.
- For best results, use a light-colored muffin tin to avoid over-caramelizing the sugar.
Pineapple Upside-Down Sugar Cookies Variations
- Tropical Twist: Add shredded coconut to the cookie dough for extra island flavor.
- Berry Medley: Replace pineapple with sliced strawberries and blueberries for a fruity variation.
- Spice It Up: Add a pinch of ground cinnamon or ginger to the dough for a warm spice note.
Equipment Needed for Pineapple Upside-Down Sugar Cookies
- Standard 12-cup muffin tin
- Mixing bowls
- Hand mixer or stand mixer
- Measuring cups and spoons
- Wire rack
- Rubber spatula
How to Store Pineapple Upside-Down Sugar Cookies
Store cookies in an airtight container at room temperature for up to 2 days, or in the refrigerator for up to 5 days. For longer storage, wrap tightly and freeze for up to 2 months; thaw at room temperature before serving.
Serving Suggestions & Pairings for Pineapple Upside-Down Sugar Cookies
- Serve warm with a scoop of vanilla ice cream for an irresistible dessert duo.
- Pair with an iced coffee or a fruity herbal tea for a delightful afternoon treat.
- Garnish with fresh mint for a pop of color and freshness.
Pro Tips for the Best Pineapple Upside-Down Sugar Cookies
- Ensure your butter is fully softened before creaming for the fluffiest cookie texture (learn more about creaming butter and sugar).
- Let the cookies cool for just 5 minutes before inverting—too long, and they may stick.
- Use a thin offset spatula to help gently lift and invert the cookies cleanly.
Frequently Asked Questions about Pineapple Upside-Down Sugar Cookies
- Can I make Pineapple Upside-Down Sugar Cookies ahead of time?
- Yes! You can bake them a day in advance and store airtight; warm gently before serving if desired.
- Can I use fresh pineapple instead of canned?
- Absolutely—just be sure to peel, core, and finely slice or dice it, and pat it very dry before using.
- Are Pineapple Upside-Down Sugar Cookies gluten-free?
- Not as written, but you can substitute a good 1:1 gluten-free flour blend with excellent results (see tips for gluten-free baking).
Ingredients
- 1 ½ cups all-purpose flour
- ½ teaspoon baking powder
- ¼ teaspoon salt
- ½ cup unsalted butter, softened
- ¾ cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- ½ cup canned pineapple tidbits, drained and chopped
- 6 maraschino cherries, halved
- 2 tablespoons light brown sugar
Instructions
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1Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper.
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2In a medium bowl, whisk together the flour, baking powder, and salt.
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3In a large bowl, cream together the butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract.
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4Gradually add the dry ingredients to the wet ingredients, mixing until just combined.
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5Spoon about 1 tablespoon of dough onto the baking sheet for each cookie. Press a small amount of chopped pineapple and half a cherry into the center of each dough mound. Sprinkle with brown sugar.
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6Bake for 13-15 minutes, or until the edges are lightly golden. Cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.
Approximate Information for One Serving
Nutrition Disclaimers
Number of total servings shown is approximate. Actual number of servings will depend on your preferred portion sizes.
Nutritional values shown are general guidelines and reflect information for 1 serving using the ingredients listed, not including any optional ingredients. Actual macros may vary slightly depending on specific brands and types of ingredients used.
To determine the weight of one serving, prepare the recipe as instructed. Weigh the finished recipe, then divide the weight of the finished recipe (not including the weight of the container the food is in) by the desired number of servings. Result will be the weight of one serving.
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