If you adore the nostalgic charm of classic pineapple upside-down cake but want a fun, handheld twist, this Pineapple Upside-Down Cookies Recipe is going to become your new favorite treat. These delightful little cookies capture the sweet caramelized pineapple and cherry topping perfectly, while surrounding it all with a tender, buttery cookie that’s simply irresistible. Whether for a cozy afternoon snack or a charming party dessert, these cookies bring sunshine and smiles in every bite.
Ingredients You’ll Need
These ingredients are straightforward pantry staples that combine to create layers of flavor, texture, and that iconic pineapple upside-down look. Each component is carefully chosen to ensure the cookies are moist, flavorful, and beautifully presented.
- Unsalted butter: Essential for both the rich topping and the tender cookie dough, providing a silky mouthfeel and depth of flavor.
- Light brown sugar: Adds a lovely caramel note in the topping and cookie dough, enhancing sweetness with a touch of molasses.
- Canned pineapple rings: The star of the show, offering juicy tropical brightness that caramelizes beautifully during baking.
- Maraschino cherries: For that classic, vibrant pop of color and a sweet, slightly tart contrast.
- Granulated sugar: Helps create a light texture and balances the brown sugar’s richness.
- Eggs: Bind the dough and add richness, keeping the cookies moist and soft.
- Vanilla extract: Enhances all the flavors with a warm, sweet aroma.
- Sour cream: Makes the cookie dough tender and adds a subtle tang that complements the pineapple perfectly.
- All-purpose flour: The structural base of your cookies, balancing softness and stability.
- Baking powder and baking soda: These leavening agents give the cookies a light lift and perfect crumb.
- Salt: Enhances the sweetness and balances flavors.
- Cornstarch: Keeps the cookies tender by softening the gluten bite.
How to Make Pineapple Upside-Down Cookies Recipe
Step 1: Prepare Your Oven and Pan
Start by preheating your oven to a warm 350°F (175°C). While that heats up, lightly grease or spray a muffin pan—this creates the perfect base for each cookie’s topping, ensuring easy release after baking.
Step 2: Layer the Topping
Into each muffin cup, pour a teaspoon each of melted butter and brown sugar. This little caramel base will bubble up and coat the pineapple beautifully. Then, arrange a halved pineapple ring with a maraschino cherry nestled in the center—this classic combo is what gives these cookies their irresistible look and taste.
Step 3: Make the Cookie Dough
In a large bowl, beat your softened butter with granulated and brown sugars until the mixture fluffs up light and creamy. Add eggs one at a time, beating well after each addition, then stir in vanilla extract and sour cream until everything is fully combined. In a separate bowl, whisk the flour, baking powder, baking soda, salt, and cornstarch to evenly distribute the leavening.
Step 4: Combine Wet and Dry Ingredients
Gradually add your dry ingredients to the wet mixture, folding just until a soft dough forms. Avoid overmixing to keep the cookies tender and melt-in-your-mouth.
Step 5: Assemble and Bake
Spoon or scoop the cookie dough on top of each pineapple ring and cherry combo, filling cups nearly to the top. Pop the pan into the oven and bake for 18 to 22 minutes, until cookies turn golden and set around the edges.
Step 6: Cool and Invert
After baking, let the cookies cool in the pan for about 10 minutes. Then carefully flip the pan over onto a wire rack—the magic moment when the caramelized pineapple topping reveals itself in all its glory!
How to Serve Pineapple Upside-Down Cookies Recipe
Garnishes
Consider a light dusting of powdered sugar for a snowy touch or a dollop of whipped cream to add luscious creaminess that complements the caramel and tropical flavors perfectly.
Side Dishes
These cookies pair wonderfully with a cup of hot tea or coffee, making for an inviting afternoon treat. For a refreshing balance, serve alongside fresh fruit or a simple vanilla ice cream scoop.
Creative Ways to Present
Try stacking the cookies on a decorative platter layered with pineapple leaves for an eye-catching tropical display. Or place them in small paper liners with a cherry on top for an adorable party favor that guests will love.
Make Ahead and Storage
Storing Leftovers
Store any leftover Pineapple Upside-Down Cookies in an airtight container at room temperature for up to three days. This keeps them soft while the topping stays moist and flavorful.
Freezing
For longer storage, freeze the cookies individually on a baking sheet, then transfer them to a zip-top bag. They keep well for up to two months, perfect for making ahead or saving a batch for later.
Reheating
Warm frozen or room temperature cookies in a preheated oven at 300°F (150°C) for about 5 to 7 minutes to revive that fresh-baked texture and aroma. Avoid microwaving, as it can make the cookie base chewy.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Just trim and slice fresh pineapple rings to fit your muffin cups. Keep in mind fresh pineapple has more moisture, so gently pat slices dry to prevent soggy bottoms.
Are these cookies gluten-free?
This recipe uses all-purpose flour, so it’s not gluten-free as is. However, you can experiment with gluten-free flour blends for a similar texture, though results may vary.
Can I make these cookies vegan?
You can swap out butter for plant-based margarine and use flax eggs or other egg substitutes. Sour cream can be replaced with vegan alternatives like coconut yogurt, though the taste and texture will be slightly different.
What’s the best way to ensure the topping doesn’t stick?
Make sure to grease your muffin pan well. Using melted butter and spraying the molds beforehand provides a slick surface that lets the cookies release effortlessly after baking and flipping.
Can I double the recipe for a larger batch?
Yes! Just double all ingredients and bake in batches if needed. Be sure not to overcrowd your oven for even cooking and crisp edges.
Final Thoughts
There is something truly magical about the combination of caramelized pineapple and a soft cookie dough that makes this Pineapple Upside-Down Cookies Recipe unforgettable. It channels the nostalgia of a classic dessert while giving you the convenience of a perfect little cookie. I highly encourage you to give this recipe a try and share the joy it brings with your friends and family—it’s sure to brighten any day with a sweet, tropical hug!
Print
Pineapple Upside-Down Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 22 minutes
- Total Time: 42 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
These Pineapple Upside-Down Cookies combine the classic flavors of the iconic dessert with the convenience and fun of individual cookie portions. Featuring a buttery brown sugar and pineapple topping, crowned with maraschino cherries, and a soft, tender cookie dough baked on top, these cookies offer a delightful blend of caramelized sweetness and rich vanilla-infused dough, perfect for gatherings or a special treat.
Ingredients
Topping Layer
- 1/2 cup unsalted butter, melted
- 1/2 cup light brown sugar
- 6 canned pineapple rings, halved or trimmed to fit molds
- 6 maraschino cherries
Cookie Dough
- 1 cup unsalted butter, room temperature
- 1 cup granulated sugar
- 1/2 cup packed light brown sugar
- 2 large eggs
- 1 tsp vanilla extract
- 1/2 cup sour cream
- 3 cups all-purpose flour
- 1 tsp baking powder
- 1/2 tsp baking soda
- 1/4 tsp salt
- 2 tsp cornstarch
Instructions
- Preheat Oven: Preheat your oven to 350°F (175°C) to ensure it’s at the perfect temperature for baking the cookies evenly.
- Prepare Muffin Pan: Lightly grease or spray a muffin pan to prevent sticking. This helps the cookies release easily once baked.
- Add Topping Base: Into each muffin cup, pour 1 teaspoon of melted butter followed by 1 teaspoon of light brown sugar. This mixture will caramelize during baking to create the classic upside-down effect.
- Place Pineapple and Chic Cherry: Place a halved pineapple ring and a maraschino cherry in the center of each muffin cup, pressing down slightly to adhere to the sugar mixture.
- Mix Wet Ingredients: In a large bowl, beat the softened unsalted butter with granulated sugar and brown sugar until fluffy and creamy. This incorporates air for lightness.
- Add Eggs and Flavor: Add eggs one at a time to the butter and sugar mixture, mixing well after each addition. Then blend in the vanilla extract and sour cream to enrich the dough and add moisture.
- Combine Dry Ingredients: In a separate bowl, whisk together all-purpose flour, baking powder, baking soda, salt, and cornstarch. These leaveners and starch help the cookies rise and keep them tender.
- Mix Dry into Wet: Gradually add the dry ingredients into the wet mixture, stirring until a soft dough forms. Avoid overmixing to maintain tender texture.
- Fill Muffin Cups: Spoon or scoop the cookie dough over the pineapple and cherry in each muffin cup, filling nearly to the top to cover the fruit completely.
- Bake: Bake the cookies in the preheated oven for 18 to 22 minutes, or until they are golden brown on top and set in the middle.
- Cool and Invert: After baking, let the cookies cool in the pan for 10 minutes. Then carefully invert the muffin pan onto a wire rack to release the cookies and reveal the caramelized pineapple and cherry topping.
Notes
- Ensure butter for the dough is softened to room temperature for easy mixing and a smooth cookie texture.
- Carefully invert the muffin pan after cooling to prevent the topping from sticking or breaking.
- Pineapple rings can be trimmed to fit perfectly into muffin cups for even coverage.
- Store the cookies in an airtight container at room temperature for up to 3 days.
- For a tangier flavor, consider substituting the sour cream with Greek yogurt.
