Pineapple Upside Down Sugar Cookies

Looking for a fun, tropical twist on a classic cookie? These Pineapple Upside Down Sugar Cookies combine the buttery sweetness of sugar cookies with the caramelized goodness of pineapple, creating a delightful treat you won’t be able to resist!

Imagine soft, chewy sugar cookies topped with juicy pineapple slices, brown sugar, and a caramelized finish. Each bite brings the perfect balance of sweet, tart, and buttery flavors with a touch of tropical flair.

These cookies are the ultimate fusion of two beloved desserts: sugar cookies and pineapple upside-down cake. Perfect for summer gatherings, family treats, or anytime you want something a little different yet familiar!

Ready to bake up these irresistible cookies? Let’s make Pineapple Upside Down Sugar Cookies and enjoy a tropical twist on a classic favorite today!

Why You’ll Love This Recipe

• Tropical Twist: The bright flavor of pineapple with sweet cherries makes these cookies cheerful and fun.
• Soft & Buttery Texture: These sugar cookies are soft in the middle with caramelized bottoms, thanks to the brown sugar and butter.
• Simple Ingredients: No fancy tools or hard-to-find ingredients needed—just pantry staples and canned pineapple.
• Crowd-Pleaser: Great for birthdays, BBQs, or just when you want something different than chocolate chip.

What You Need to Know Before You Start

Prep Time & Cook Time:
Prep Time: 25 minutes
Bake Time: 12–14 minutes
Total Time: About 40 minutes

Servings:
Makes about 13–14 cookies (using one pineapple ring and one cherry per cookie)

Difficulty:
Easy for beginners. No mixer needed if you want to mix by hand. Fun to make with kids, too.

Required Kitchen Tools

• Muffin tin (standard size, 12-cup or more)
• Mixing bowls
• Whisk or hand mixer
• Spatula or spoon
• Measuring cups and spoons
• Sharp knife and cutting board
• Cooling rack

Ingredients for Pineapple Upside Down Sugar Cookies

You’ll need two sets of ingredients—one for the topping and one for the cookie dough. Each piece plays a role in flavor and texture.

For the Topping:

• 13 canned pineapple slices (cut in half if needed to fit)
• 13 maraschino cherries
• 1/2 cup (113g) unsalted butter, melted
• 1 cup (200g) light brown sugar, packed

For the Sugar Cookie Dough:

• 1 cup (226g) butter, room temperature
• 1 and 1/2 cups (300g) granulated sugar
• 2 large eggs
• 1/2 cup (120g) sour cream
• 3 cups (375g) all-purpose flour, spooned and leveled
• 1 tsp baking powder
• 1 tsp vanilla extract
• 1/2 tsp salt

How to Make Pineapple Upside Down Sugar Cookies: Step-by-Step Instructions

1. Prepare the Topping

1. Grease your muffin tin generously with butter or nonstick spray.
2. In a small bowl, stir the melted butter and brown sugar together until it looks like wet sand.
3. Spoon about 1 tablespoon of this butter-sugar mixture into the bottom of each muffin cup.
4. Place 1 pineapple slice (cut to fit, if needed) on top of the mixture.
5. Nestle 1 maraschino cherry in the center of each pineapple ring. Set aside.

Tip: If the pineapple slices are too large for the muffin wells, cut them in half or into smaller rings.

2. Make the Sugar Cookie Dough

1. In a large bowl, cream the softened butter and granulated sugar until light and fluffy (about 2–3 minutes with a hand mixer, or longer by hand).
2. Add in the eggs one at a time, mixing well after each one.
3. Mix in the sour cream and vanilla extract until smooth.
4. In another bowl, whisk together flour, baking powder, and salt.
5. Gradually add the dry ingredients to the wet ingredients. Stir just until combined—don’t overmix.

3. Assemble the Cookies

1. Scoop about 2 tablespoons of cookie dough and flatten slightly with your hands.
2. Gently press the dough over the pineapple and cherry in each muffin cup. The dough should completely cover the fruit.
3. Smooth the tops so they bake evenly.

4. Bake

1. Preheat oven to 350°F (177°C).
2. Bake for 12–14 minutes, or until the edges are lightly golden. The centers will look soft but set as they cool.
3. Remove from the oven and let cool in the pan for 10 minutes.

Important: Do not skip the cooling time. This helps the sugar topping firm up just enough for clean removal.

5. Unmold the Cookies

1. Run a knife around each cookie to loosen.
2. Carefully invert the muffin tin onto a baking sheet or cooling rack. Give it a gentle tap if needed.
3. Let the cookies cool completely before serving.

Serving and Decoration

These cookies are best served slightly warm or at room temperature. When flipped out of the pan, each cookie has a glossy pineapple slice and a bright cherry right on top—no need for extra decorating.

Ideas for Serving:

• Party trays: Serve them on a white platter to let the colors pop.
• With whipped cream: A dollop on the side adds a soft, creamy contrast.
• As dessert bites: Pair with coffee, tea, or a scoop of vanilla ice cream.

Storage and Make-Ahead Tips

• Room Temperature: Store in an airtight container for up to 2 days.
• Refrigerator: For longer storage (up to 5 days), refrigerate and bring to room temp before serving.
• Freezer: You can freeze the cookies (after flipping) in a single layer, then stack with parchment paper between them in a zip-top bag for up to 1 month.

Reheat in the microwave for 10–15 seconds to bring back that soft texture and warm flavor.

Variations

• Mini Version: Use mini muffin tins and chopped pineapple for bite-size treats.
• Add Coconut: Mix 1/2 cup shredded coconut into the cookie dough for extra texture.
• Gluten-Free Option: Use a 1:1 gluten-free flour blend.
• Spiced Version: Add a pinch of cinnamon or nutmeg to the dough for a cozy twist.

Tips and Tricks for Success

• Dry the pineapple and cherries slightly before placing them in the pan to reduce sogginess.
• Chill the dough for 15–20 minutes if it’s too sticky to handle.
• Don’t overbake—the cookies should look pale on top. The caramelized base will finish setting after cooling.
• Flip while warm, but not hot—waiting 10 minutes is key for easy release.

Nutrition

Nutrient	Per Cookie (Approx.)
Calories	220
Total Fat	11g
Saturated Fat	7g
Cholesterol	40mg
Sodium	80mg
Total Carbohydrates	29g
Dietary Fiber	<1g
Sugars	19g
Protein	2g

Note: Nutrition values are estimates and may vary depending on ingredient brands and portion size.

Pineapple Cookie FAQs

Can I use fresh pineapple instead of canned?
Yes, just slice it thin and remove extra juice with a paper towel.

What if the cookies stick to the muffin tin?
Make sure to grease well and let them rest 10 minutes before flipping. A silicone spatula can help loosen edges gently.

Can I make the dough ahead of time?
Yes, the dough can be stored in the fridge for up to 24 hours before baking.

Conclusion

These Pineapple Upside Down Sugar Cookies are sweet, simple, and packed with tropical charm. Whether you’re baking for a party or just need a little escape in dessert form, these cheerful cookie cups will brighten any day. Try them once, and they might just become your new favorite twist on sugar cookies.