If you have a sweet spot for nostalgic desserts with a tropical twist, then you are absolutely going to love this Pineapple Upside-Down Cookies Recipe. These little delights capture the charm and caramelized goodness of the classic cake but shrink it down into perfectly individual cookie-sized treats. Imagine golden, buttery cookies with a gooey brown sugar glaze, topped with a ring of juicy pineapple and a bright maraschino cherry that pops with every bite. Whether for a party, an afternoon pick-me-up, or just because, these cookies bring sunshine and smiles to any occasion.
Ingredients You’ll Need
To create the magic of this Pineapple Upside-Down Cookies Recipe, you don’t need a long list of fancy ingredients—just simple, quality staples that each play a crucial role. From rich butter providing tenderness, to the tangy sour cream keeping the cookies moist, and the sweet pineapple rings lending that iconic tropical flair, every component is essential.
- 1 cup butter, room temperature: Adds richness and a tender crumb to the cookies.
- 1 ½ cups granulated sugar: Sweetens the dough and helps with browning during baking.
- 2 eggs: Bind the ingredients together and give structure.
- 2 teaspoons vanilla extract: Enhances the overall flavor with a warm, comforting note.
- ½ cup sour cream: Adds moisture and a slight tang for balance.
- 3 cups all-purpose flour: The base that holds everything together.
- 1 teaspoon baking powder: Helps the cookies rise softly.
- 1 teaspoon cornstarch: Contributes to a tender, melt-in-your-mouth texture.
- ½ teaspoon salt: Elevates the sweetness and deepens flavor complexity.
- 13 canned pineapple slices: The star piece that gives the cookie its name and tropical sweetness.
- 13 maraschino cherries: Adds a burst of color and bright sweetness on top.
- ½ cup butter, melted: Mixed with brown sugar to create the sticky, caramelized base.
- 1 cup light brown sugar, packed: Gives that classic rich, molasses flavor with a touch of chewiness.
How to Make Pineapple Upside-Down Cookies Recipe
Step 1: Preheat and Prepare Your Pans
Start by preheating your oven to 350°F (175°C), setting the stage for perfectly baked cookies. While the oven warms up, prepare a mini round cake pan—it’s ideal for shaping these individual cookie portions and managing the delightful pineapple topping.
Step 2: Cream Butter and Sugar
In a large mixing bowl, cream together the room temperature butter and granulated sugar until the mixture turns light and fluffy. This step is key since it incorporates air, ensuring your cookies will have a tender and soft texture. Then beat in the eggs, vanilla extract, and sour cream until everything is well combined and silky smooth, blending moisture and flavor seamlessly.
Step 3: Mix Dry Ingredients
In a separate bowl, whisk together the flour, baking powder, cornstarch, and salt. Mixing the dry components thoroughly before adding them to the wet ingredients helps your cookies rise evenly and keeps them tender but structured.
Step 4: Combine Wet and Dry Ingredients
Gradually introduce the dry mixture into the wet, stirring gently just until combined. It’s super important not to over-mix here since that can make the cookies tough rather than soft and crumbly—easy does it for that perfect cookie texture.
Step 5: Prepare the Caramel Base and Fruit Topping
Mix the melted butter with the brown sugar until you get a smooth, rich caramel mixture. Spoon about one tablespoon of this onto the bottom of each cavity in your mini cake pan, spreading it evenly. Then place a pineapple slice on top of each caramel base, followed by a maraschino cherry right in the center. This sweet layer will become wonderfully gooey and fragrant as it bakes under the cookie dough.
Step 6: Add Cookie Dough
Scoop roughly three tablespoons of cookie dough over each pineapple slice. Use an offset spatula or the back of a spoon to flatten the dough evenly so it covers the fruit and caramel layers completely. This step ensures the pineapple stays in place and the cookie bakes uniformly.
Step 7: Bake to Golden Perfection
Slide the prepared pan into your oven and bake for about 25 minutes. Look for golden edges and the bubbly brown sugar mixture oozing slightly up the sides of each cookie—this is when you know they’re perfectly caramelized and ready to come out.
Step 8: Cool and Unmold Carefully
Once baked, let the cookies cool in the pan for 10 minutes to set. Then gently turn them out onto a wax paper-covered surface to catch any drips. If any pineapple slices stick to the pan, carefully reposition them on the cookies while still warm—this keeps every cookie picture-perfect and delicious.
How to Serve Pineapple Upside-Down Cookies Recipe
Garnishes
For an almost-too-pretty-to-eat presentation, consider dusting your Pineapple Upside-Down Cookies with a tiny sprinkle of powdered sugar or a light drizzle of melted white chocolate. Fresh mint leaves can add a pop of green and a refreshing contrast to that buttery sweetness.
Side Dishes
These cookies pair wonderfully with a scoop of vanilla ice cream or a dollop of whipped cream, turning them into an indulgent dessert. For a brighter contrast, serve alongside a fresh fruit salad or tropical punch to complement the pineapple’s sunny flavor.
Creative Ways to Present
Try arranging the cookies on a pretty platter lined with pineapple leaves for a tropical themed party. You can also stack them in a dessert tower for gatherings or package them in clear cellophane bags tied with a cheerful ribbon—they make fantastic handmade gifts that scream homemade love.
Make Ahead and Storage
Storing Leftovers
Once completely cooled, store your Pineapple Upside-Down Cookies in an airtight container at room temperature. They will stay fresh and delicious for up to 3 days, and the caramelized pineapple topping keeps the cookies moist and flavorful.
Freezing
You can freeze these cookies to enjoy later! Place them in a single layer on a baking sheet to freeze initially, then transfer them to a freezer-safe container or bag. They’ll keep beautifully for up to 3 months without losing texture or flavor.
Reheating
Reheat frozen or room temperature cookies in a preheated oven at 300°F (150°C) for about 5 minutes. This simple step revives that warm, gooey feeling and melts the caramel topping back to its irresistible state.
FAQs
Can I use fresh pineapple instead of canned?
Fresh pineapple can work, but canned slices have the perfect thickness and sweetness that crisps up nicely in this recipe. If you use fresh, be sure to slice them evenly and pat them dry to avoid soggy cookies.
What if I don’t have mini round cake pans?
If you don’t have mini round pans, try using a mini muffin tin or even regular muffin tins lined with cupcake liners. The size and shape might differ slightly, but the cookies will still taste fantastic.
Can I substitute sour cream?
If you’re out of sour cream, plain Greek yogurt is an excellent substitute. It will provide the same tanginess and moisture, keeping the cookies tender and flavorful.
How do I prevent the pineapple from sticking to the pan?
Greasing the pan thoroughly and using the brown sugar-butter mixture at the bottom helps create a natural release layer. Also, let the cookies cool slightly in the pan before turning them out.
Are these cookies gluten-free?
This recipe uses all-purpose flour, which contains gluten. To make them gluten-free, swap in a gluten-free all-purpose flour blend that includes xanthan gum to help retain texture.
Final Thoughts
There is something undeniably joyful about making and sharing the Pineapple Upside-Down Cookies Recipe. Each bite carries that perfect harmony of buttery cookie, rich caramel, and sunny pineapple that lights up your taste buds and your day. Whether you’re baking them for family, friends, or just yourself, these cookies bring warmth, nostalgia, and tropical sweetness in every delicious mouthful. Go ahead, give this recipe a whirl—your kitchen will thank you!
Print
Pineapple Upside-Down Cookies Recipe
- Prep Time: 10 minutes
- Cook Time: 25 minutes
- Total Time: 35 minutes
- Yield: 13 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
These Pineapple Upside-Down Cookies are a delightful twist on the classic dessert, featuring a caramelized brown sugar and butter base topped with juicy pineapple slices and maraschino cherries. Soft, buttery cookie dough is baked atop the fruit, creating a beautiful and tasty treat perfect for any occasion.
Ingredients
Cookie Dough
- 1 cup butter, room temperature
- 1 ½ 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
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup butter, melted
- 1 cup light brown sugar, packed
Instructions
- Preheat and Prepare: Preheat the oven to 350°F (175°C). Prepare a mini round cake pan by setting it aside, ready for layering and baking.
- Cream Butter and Sugar: In a large mixing bowl, cream together the room temperature butter and granulated sugar until light and fluffy. Beat in the eggs, vanilla extract, and sour cream until well combined, forming the wet cookie dough base.
- Mix Dry Ingredients: In another bowl, whisk together the all-purpose flour, baking powder, cornstarch, and salt to ensure an even distribution of leavening agents and flavor.
- Combine Wet and Dry: Gradually mix the dry ingredients into the wet ingredients until just combined. Take care not to over-mix to keep the dough tender.
- Prepare Topping Layer: In a separate bowl, combine the melted butter with the brown sugar until smooth. Spoon about a tablespoon of this brown sugar mixture into the bottom of each cake pan cavity, spreading it evenly to form the caramel base. Place a pineapple slice over the brown sugar layer, and add a maraschino cherry in the center of each pineapple slice.
- Add Cookie Dough: Scoop approximately 3 tablespoons of cookie dough on top of each pineapple slice. Use an offset spatula to flatten the dough evenly over the fruit, ensuring full coverage.
- Bake: Bake in the preheated oven for about 25 minutes, or until the edges turn golden and the brown sugar mixture bubbles up the sides, creating a caramelized effect.
- Cool and Remove: Allow the cookies to cool in the pan for 10 minutes before carefully turning them out onto a wax paper-covered surface to catch any sticky drips from the brown sugar. If any pineapple slices stick to the pan, gently reposition them on the cookies. Let the cookies cool completely before serving.
Notes
- Use an offset spatula for even spreading of the dough over the pineapple slices.
- Do not over-mix the dough to ensure tender, soft cookies.
- Cooling the cookies in the pan before removing helps prevent them from breaking apart.
- Reposition any pineapple slices that stick to the pan after flipping for a perfect presentation.
- These cookies can be stored in an airtight container at room temperature for up to 3 days.
