These Pineapple Upside Down Cookies are a fun, bite-sized twist on the classic cake! Soft, buttery cookies are topped with caramelized pineapple slices, bringing the same sweet and tangy flavors in a handheld treat. Perfect for parties, holidays, or summer gatherings!
Why You’ll Love This Recipe
- A fun take on pineapple upside-down cake
- Soft, buttery, and full of flavor
- Perfect for parties or individual servings
- Easy to make with simple ingredients
- Tropical flavors in every bite
Ingredients
(Tip: You can find the complete list of ingredients and their measurements in the recipe card below.)
For the Cookies:
- 1 cup butter (room temperature)
- 1½ cups granulated sugar
- 2 eggs
- 2 teaspoons vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon cornstarch
- ½ teaspoon salt
For the Topping:
- 13 canned pineapple slices (drained and patted dry)
- ½ cup brown sugar
- ¼ cup melted butter
Directions
1. Prepare the Topping
- Preheat oven to 350°F (175°C).
- Grease or line a baking sheet with parchment paper.
- In a small bowl, mix melted butter and brown sugar.
- Place a small amount of the mixture onto the baking sheet where each cookie will go.
- Add a pineapple slice on top of the sugar mixture.
2. Make the Cookie Dough
- In a large bowl, cream butter and sugar until light and fluffy.
- Add eggs, vanilla, and sour cream, mixing well.
- In a separate bowl, whisk together flour, baking powder, cornstarch, and salt.
- Gradually mix dry ingredients into the wet ingredients until fully combined.
3. Assemble & Bake
- Scoop cookie dough onto the center of each pineapple slice, slightly flattening the dough.
- Bake for 12-15 minutes, or until cookies are golden brown.
- Let cool for 5 minutes, then carefully flip cookies upside down onto a wire rack.
4. Serve & Enjoy
- Serve warm or at room temperature.
- Optionally, drizzle with caramel sauce or sprinkle with powdered sugar.
Servings and Timing
- Servings: 13 cookies
- Prep Time: 15 minutes
- Bake Time: 12-15 minutes
- Total Time: 30 minutes
Variations
- Cherry Topping: Add a maraschino cherry in the center of each pineapple slice.
- Coconut Flavor: Mix ¼ cup shredded coconut into the cookie dough.
- Spiced Cookies: Add ½ teaspoon cinnamon for a warm twist.
- Mini Version: Cut pineapple slices into small pieces and make bite-sized cookies.
Storage & Freezing
- Refrigeration: Store in an airtight container for up to 3 days.
- Freezing: Freeze baked cookies for up to 2 months. Thaw before serving.
- Reheating: Warm in a microwave for 10-15 seconds for a fresh-baked taste.
FAQs
1. Can I use fresh pineapple?
Yes! Just slice thinly and remove excess juice before using.
2. How do I prevent the cookies from sticking?
Use parchment paper or grease the baking sheet well.
3. Can I make the dough ahead of time?
Yes! Chill the dough for up to 24 hours before baking.
4. Can I use a sugar substitute?
Yes! Replace sugar with a 1:1 sugar substitute like monk fruit sweetener.
5. How do I get a crispier cookie?
Bake for an additional 2-3 minutes for a firmer texture.
6. Can I make these gluten-free?
Yes! Use gluten-free all-purpose flour for a GF version.
7. Can I use a different fruit?
Try peach slices or apple rings for a unique variation.
8. Do these cookies need to be flipped?
Yes! Flipping them after baking helps reveal the caramelized pineapple topping.
9. How do I keep them from getting soggy?
Pat the pineapple slices completely dry before baking.
10. Can I add nuts?
Yes! Sprinkle chopped pecans or almonds on top for crunch.
Conclusion
These Pineapple Upside Down Cookies are a fun, tropical take on a classic dessert. With buttery cookie dough and caramelized pineapple, they’re the perfect balance of soft, chewy, and fruity. Try them today and enjoy a taste of the tropics in every bite!
Print
- Total Time: 30 minutes
- Yield: 13 cookies 1x
- Diet: Vegetarian
Description
These Pineapple Upside-Down Cookies bring all the flavors of the classic cake into a bite-sized treat! Featuring a buttery vanilla cookie base, tangy pineapple slices, and a caramelized topping, these cookies are soft, chewy, and bursting with tropical flavor—perfect for any occasion!
Ingredients
For the Cookie Dough:
- 1 cup butter, room temperature
- 1 1/2 cups granulated sugar
- 2 large eggs
- 2 teaspoons vanilla extract
- 1/2 cup sour cream
- 3 cups all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon cornstarch
- 1/2 teaspoon salt
For the Pineapple Topping:
- 13 canned pineapple slices, drained and patted dry
- 1/2 cup brown sugar (optional, for caramelization)
Instructions
Step 1: Preheat & Prep
- Preheat oven to 350°F (175°C).
- Line a baking sheet with parchment paper.
Step 2: Make the Cookie Dough
- In a large mixing bowl, beat butter and sugar until light and fluffy.
- Add eggs, vanilla extract, and sour cream, mixing until well combined.
- In a separate bowl, whisk together flour, baking powder, cornstarch, and salt.
- Gradually add dry ingredients to the wet mixture, mixing until a soft dough forms.
Step 3: Assemble the Cookies
- Scoop tablespoon-sized portions of dough onto the baking sheet, spacing them 2 inches apart.
- Press a pineapple slice gently into the center of each cookie.
- Sprinkle brown sugar over the pineapple slices for a caramelized finish (optional).
Step 4: Bake & Cool
- Bake for 12-15 minutes, or until cookies are set and lightly golden around the edges.
- Let cool for 5 minutes on the baking sheet before transferring to a wire rack.
Serving & Storage:
- Serve warm or at room temperature for the best flavor.
- Store in an airtight container at room temperature for up to 3 days or refrigerate for up to 5 days.
Notes
- For extra caramelization, brush pineapple slices with melted butter and brown sugar before baking.
- Make them extra tropical by adding ¼ cup shredded coconut to the cookie dough!
- Want a cherry on top? Place a maraschino cherry in the center of each pineapple slice before baking.
- Prep Time: 15 minutes
- Cook Time: 15 minutes
- Category: Desserts
- Method: Baking
- Cuisine: American
