Pineapple Upside-Down Sugar Cookies bring the nostalgic flavors of a classic pineapple upside-down cake into a fun, handheld treat. These bright, buttery cookies combine caramelized brown sugar, juicy pineapple, and a soft sugar-cookie base for a dessert that’s both comforting and delightfully fresh.
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Perfect for parties, bake sales, family gatherings, or whenever you’re craving a tropical-inspired treat, this recipe delivers amazing flavor with simple ingredients. Each cookie is topped with golden pineapple and a cherry, creating a beautiful presentation with minimal effort. If you enjoy classic desserts with a playful twist, this recipe is sure to become a new favorite.
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Ingredients
For the Cookie Dough
- 2 cups all-purpose flour
- 1 cup granulated sugar
- 1/2 cup unsalted butter, softened
- 1 large egg
- 1 teaspoon baking powder
- 1/4 teaspoon salt
For the Topping
- 6 canned pineapple rings (cut in half for 12 cookies)
- 1/2 cup brown sugar
- 12 maraschino cherries
Instructions
Step 1: Prep
- Preheat oven to 350°F (175°C).
- Line a baking sheet with parchment paper.
Step 2: Make the Cookie Dough
- In a large bowl, cream the softened butter and granulated sugar until light and fluffy.
- Mix in the egg until fully combined.
- Add flour, baking powder, and salt. Stir until the dough forms and pulls together.
Step 3: Assemble the Cookies
- Sprinkle a spoonful of brown sugar onto the center of each pineapple half.
- Place a maraschino cherry in the middle of each piece.
- Set the pineapple pieces cherry-side down on the baking sheet.
- Scoop cookie dough over each pineapple piece, gently pressing to cover the back.
Step 4: Bake
- Bake for 12–15 minutes, or until the cookies are lightly golden around the edges.
- Allow them to cool for at least 10 minutes before lifting gently from the tray.
- Serve warm or at room temperature.
Pro Tips
- Pat pineapple slices dry to prevent excess moisture in the cookies.
- Chill the dough for 10–15 minutes for thicker, chewier cookies.
- Use a cookie scoop for even portions.
- Flip carefully—use a spatula to keep the topping intact.
Why This Recipe Works
- Perfect flavor balance: Sweet brown sugar caramelizes beautifully with tangy pineapple.
- Easy to make: Uses pantry staples and one bowl for the dough.
- Crowd-pleasing presentation: Each cookie looks like a mini upside-down cake.
- Fun twist: A creative way to reinvent a nostalgic dessert.
Substitutions & Variations
Fruit Variations
- Swap pineapple for peaches, mango, or apple slices.
- Use fresh pineapple instead of canned.
Baking Alternatives
- Replace flour with a 1:1 gluten-free blend.
- Use coconut sugar instead of brown sugar for a deeper flavor.
Flavor Add-Ons
- Add 1 teaspoon vanilla extract to the dough.
- Sprinkle toasted coconut on top after baking.
- Add a pinch of cinnamon to the brown sugar topping.
Make-Ahead, Storage & Reheating Guide
Make-Ahead
- Dough can be prepared 48 hours ahead and chilled.
- Assemble cookies just before baking.
Storage
- Store in an airtight container for 3–4 days.
- Keep in the refrigerator for up to 1 week.
Freezing
- Freeze baked cookies for up to 2 months.
- Thaw at room temperature.
Reheating
- Warm in the microwave for 8–10 seconds for soft, bakery-style texture.
Serving Ideas
- Serve with vanilla or coconut ice cream.
- Add a drizzle of caramel sauce for an extra treat.
- Pair with iced tea, lemonade, or a warm cup of tea.
- Serve warm at brunch or as a summer dessert.
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Nutrition (Per Serving Estimate)
- Calories: 220
- Fat: 8g
- Carbohydrates: 35g
- Protein: 2g
- Fiber: 1g
- Sugar: 20g
- Sodium: 130mg
Frequently Asked Questions
Can I use fresh pineapple?
Yes! Just slice it thinly so it caramelizes easily.
Why did my cookies spread too much?
Your dough may have been too warm—chill for 15 minutes next time.
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Can I double the recipe?
Absolutely. This recipe scales very well.
Do the cookies need to cool completely?
Cooling helps them hold together, but they taste great warm too.
These Pineapple Upside-Down Sugar Cookies deliver everything you love about the classic cake in a charming, portable cookie form. With buttery dough, caramelized pineapple, and a burst of cherry sweetness, every bite is a treat. Simple, fun, and perfect for any occasion—this recipe is sure to become a go-to favorite in your kitchen.
Easy Pineapple Upside-Down Sugar Cookies
Ingredients
For the Cookie Dough
- 2 cups all-purpose flour
- 1 cup granulated sugar
- 1/2 cup unsalted butter, softened
- 1 large egg
- 1 tsp baking powder
- 1/4 tsp salt
For the Topping
- 6 canned pineapple rings (cut in half for 12 cookies)
- 1/2 cup brown sugar
- 12 maraschino cherries
Instructions
Step 1: Prep
- Preheat oven to 350°F (175°C).
- Line a baking sheet with parchment paper.
Step 2: Make the Cookie Dough
- In a large bowl, cream the softened butter and granulated sugar until light and fluffy.
- Mix in the egg until fully combined.
- Add flour, baking powder, and salt. Stir until the dough forms and pulls together.
Step 3: Assemble the Cookies
- Sprinkle a spoonful of brown sugar onto the center of each pineapple half.
- Place a maraschino cherry in the middle of each piece.
- Set the pineapple pieces cherry-side down on the baking sheet.
- Scoop cookie dough over each pineapple piece, gently pressing to cover the back.
Step 4: Bake
- Bake for 12–15 minutes, or until the cookies are lightly golden around the edges.
- Allow them to cool for at least 10 minutes before lifting gently from the tray.
- Serve warm or at room temperature.
Notes
- Use room-temperature butter for the best cookie texture.
- If the cookies stick, let them cool longer before lifting.
- Make the cookies smaller by cutting pineapple rings into thirds.
- Perfect for summer gatherings or holiday trays.
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