These pineapple upside down sugar cookies are one of the most fun desserts I’ve made in a long time. They have all the flavor of pineapple upside-down cake, but in soft, buttery cookie form with glossy caramelized pineapple on top.
In the mood for something else with pineapple? Try this no bake Pineapple Coconut Yogurt Bark.
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Try These Tropical Pineapple Cookies
I love recipes like this because they are a joy to make, and even kids can join in the fun. Each cookie is baked over caramelized pineapple and then flipped after baking so the glossy fruit topping ends up on top, making the perfect Summer treat.
What Are Pineapple Upside Down Cookies?
These cookies are inspired by classic pineapple upside-down cake.
Why You’ll Love It
- Unique dessert: They’re such a fun project to take on, not your normal cookie bake.
- Perfect Texture: You get soft, buttery cookies with juicy pineapple and a sticky caramel topping.
- Beautiful presentation: They look like they were bought at a bakery, even though they are homemade.
- Perfect for summer: The fruity pineapple flavor makes these a favorite Summer treat.
Ingredients
- Pineapple rings: I like using canned pineapple in juice because the flavor is perfect, and not too sweet.
- Dark brown sugar: This is what gives you that rich caramel topping and gives the best flavor.
- Butter: The butter is the reason the cookies are rich and soft.
- Pineapple jam: This is what adds concentrated pineapple flavor, and the dough doesn't become too wet.
- Heavy cream: Helps keep the cookies soft and gives extra flavor.
How to Make Easy Pineapple Upside Down Sugar Cookies
1. Lay the pineapple rings on paper towels and press gently to remove excess moisture.
2. Preheat the oven to 350°F (175°C) and line a baking sheet or pan with parchment paper.
3. In a small bowl, mix melted butter and brown sugar. Spoon small circles onto the baking sheet.
4. Place pineapple rings over the sugar mixture and add cherries in the centers if using.
5. In a bowl, beat butter and sugar until creamy. Add egg and vanilla extract.
6. Mix in the dry ingredients, flour, baking powder, and ¼ teaspoon salt until crumbly.
7. Stir together pineapple jam and heavy cream, then add to the cookie dough.
8. Shape dough into balls, flatten slightly, and place over the pineapple rings.
9. Bake for 15–18 minutes until they are golden.
10. Let the cookies rest for exactly 4 minutes, then carefully flip them over. You can add a cherry to the tops of these cookies.
Recipe Tips
- Drying the pineapple properly is very important. If the fruit is too wet, the caramel won’t develop properly.
- I always use parchment paper because the caramel gets sticky while baking.
- Timing matters when flipping the cookies. If you flip them too early, the caramel runs everywhere, and if you are too late, the cookies will stick.
What Can You Serve With This?
- Vanilla ice cream
- Whipped cream
- Coffee
- Iced tea
- Fresh fruit
FAQs
Yes. You can cut the pineapple rings into smaller pieces and make mini pineapple upside down cookies.
Not for this recipe. The pineapple rings are what give the cookies their classic look and shape.
Yes, though I personally think they taste best the day they’re baked, while the caramel is freshest.
Recipe
Pineapple Upside Down Sugar Cookies
Ingredients
For the Topping
- 9 small pineapple rings (or cut standard rings into smaller circles)
- ¼ cup dark brown sugar
- 3 tablespoon unsalted butter, melted
- 9 maraschino cherries (optional)
The Cookie Base
- ½ cup unsalted butter, softened
- ½ cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 1¼ cups all-purpose flour
- ½ teaspoon baking powder
- ¼ teaspoon salt
- 2 tablespoon pineapple jam
- 2 tablespoon heavy cream
Instructions
- Lay the pineapple rings on paper towels and press gently to remove excess moisture.
- Preheat the oven to 350°F (175°C) and line a baking sheet or pan with parchment paper.
- In a small bowl, mix melted butter and brown sugar. Spoon small circles onto the baking sheet.
- Place pineapple rings over the sugar mixture and add cherries in the centers if using.
- In a bowl, beat butter and sugar until creamy. Add egg and vanilla extract.
- Mix in the dry ingredients, flour, baking powder, and ¼ teaspoon salt until crumbly.
- Stir together pineapple jam and heavy cream, then add to the cookie dough.
- Shape dough into balls, flatten slightly, and place over the pineapple rings.
- Bake for 15–18 minutes until they are golden.
- Let the cookies rest for exactly 4 minutes, then carefully flip them over. You can add a cherry to the tops of these cookies.
Notes
Cooking Time and Temperature
Bake at 350°F (175°C) for 15–18 minutes until golden and bubbling around the edges.Taste & Texture
Soft buttery cookies with juicy caramelized pineapple and a glossy sweet topping.Storage, Freezing & Reheating
- Fridge: Store up to 3 days in an airtight container.
- Freezer: Freeze for up to 2 months.
- Best Served: Slightly warm or at room temperature.
Serving Recommendations
I love serving these slightly warm with vanilla ice cream. The caramelized pineapple tastes incredible with something cold and creamy.Recipe Variations and Substitutions
- Add a splash of dark rum to the caramel.
- Use Amarena cherries for a more elegant look.
- Add toasted coconut on top after baking.
Proper Storage Tips
- Store in a single layer if possible.
- Keep refrigerated because of the fruit topping.
- Warm slightly before serving for the best texture.
Pro Tips
- Dry the pineapple well.
- Use parchment paper.
- Flip while the caramel is still tacky.
Video
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