Name: Pineapple Upside Down Cookies Recipe
Prep time: 20 min
Cook time: 10 min
Total time: 30 min
Cuisine: American
Ingredients: 6 tablespoons Butter, melted; 1 cup Brown Sugar (214g); Pineapple Rings, drained; Maraschino Cherries, drained; ½ cup Butter, softened; ½ cup Granulated Sugar (100g); 1 Egg, large; 1 teaspoon Vanilla Extract; ½ cup Powdered Sugar (65g); ¼ cup Vegetable Oil; ½ teaspoon Baking Soda; ½ teaspoon Cream of Tartar; 2 cups All Purpose Flour (240g)

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If you adore the tropical sweetness of pineapple combined with the charm of a classic dessert, Pineapple Upside Down Cookies are about to become your new favorite treat. These delightful little cookies capture all the best parts of the traditional upside-down cake but in a charming, handheld form that’s perfect for sharing or keeping all to yourself. Packed with gooey pineapple rings and a bright cherry center, nestled on a soft, buttery cookie base, Pineapple Upside Down Cookies bring sunshine to any kitchen all year round. They’re simple to make, irresistibly tasty, and guaranteed to brighten your snack time or dessert plate.

Pineapple Upside Down Cookies Recipe - Recipe Image

Ingredients You’ll Need

Getting your ingredients just right is the first step to making delicious Pineapple Upside Down Cookies. Each ingredient here plays a crucial role, from the richness of butter to the subtle tang from baking soda and cream of tartar, creating a cookie that’s perfectly tender and flavorful.

Butter (½ cup softened): Adds richness and helps create a tender texture in the cookie dough.
Granulated Sugar (½ cup, 100g): Sweetens the dough and helps with gentle browning.
Egg (1 large): Binds all the ingredients while contributing moisture and richness.
Vanilla Extract (1 teaspoon): Enhances the flavor with warm, aromatic notes.
Powdered Sugar (½ cup, 65g): Lightens the dough texture and adds sweetness.
Vegetable Oil (¼ cup): Keeps the cookies moist and tender.
Baking Soda (½ teaspoon): Leavens the dough for a light and airy crumb.
Cream of Tartar (½ teaspoon): Stabilizes the cookie’s texture and gives a slight tang.
All Purpose Flour (2 cups, 240g): The foundation of the cookie’s structure.
Pineapple Rings (drained): The sweet, juicy star of the cookies that creates the “upside down” effect.
Maraschino Cherries (drained): Adds a pop of color and classic sweetness in the center of each pineapple ring.
Butter (6 tablespoons melted): Used to create the luscious brown sugar topping that caramelizes beautifully.
Brown Sugar (1 cup, 214g): Provides rich caramel flavor in the base of each cookie.

How to Make Pineapple Upside Down Cookies

Step 1: Pan Preparations

First things first, preheat your oven to 350°F so it’s ready when your dough is done. Then start by mixing the melted butter with the brown sugar in a small bowl until well combined — this mixture creates that dreamy caramel base for your cookies. Drain the pineapple rings carefully, getting rid of extra juice to avoid soggy cookies. Spoon about a tablespoon of your sugar and butter mixture into each muffin cup, then press one pineapple ring over it. Top the pineapple with a vibrant maraschino cherry right in the center to give each cookie its classic look and taste. To help the cookies bake evenly without sticking together, stagger the placement of the dough in the tins allowing space for them to spread.

Step 2: Making the Cookie Dough

In a mixing bowl, cream the softened butter and granulated sugar together until you get a light, fluffy consistency. This step builds the cookie’s structure and ensures it’s not too dense. Add the egg and vanilla extract, and keep beating for a couple more minutes to combine everything smoothly. Next, gradually add the powdered sugar and vegetable oil—this combination will turn your dough pale yellow and silky. Now, sift together the flour, baking soda, and cream of tartar before folding the dry ingredients into the wet mixture. You want a smooth dough that’s easy to shape but not sticky.

Step 3: Shaping and Baking the Cookies

Using a cookie scoop (size #24 works perfectly), portion out the dough evenly. Flatten each scoop in your palm until it’s around 3 inches in diameter—this shape matches the pineapple rings and helps seal the dough around the muffin cup. Carefully place each flattened dough piece directly on top of the pineapple and cherry in the pan, gently tucking the dough into the edges to seal in all the lovely fruit and caramel mixture. Bake your Pineapple Upside Down Cookies at 350°F for 8 to 10 minutes, until the edges turn a light golden brown and the centers lose their glossy look.

Step 4: The Big Flip

Once your timer goes off, take the pan out of the oven and immediately flip it over onto a cookie sheet lined with parchment paper. This is the magical moment when the cookies turn upside down, revealing the shiny pineapple and cherry tops with the caramelized brown sugar beneath. Give them some time to cool so they set properly, and then they’re ready to enjoy.

How to Serve Pineapple Upside Down Cookies

Garnishes

For an extra-special touch, sprinkle a tiny pinch of flaky sea salt on top after flipping. The saltiness highlights the sweetness and enhances the caramel notes beautifully. Fresh mint leaves make a lovely garnish too, adding a refreshing pop of color and aroma.

Side Dishes

Serve these cookies alongside a scoop of vanilla ice cream or a dollop of whipped cream for a luscious dessert experience. If you’re aiming for a lighter snack, pair them with a fruity iced tea or a cup of tropical-flavored coffee for an unforgettable flavor pairing.

Creative Ways to Present

Consider arranging your Pineapple Upside Down Cookies on a tiered dessert tray for parties or afternoon tea. Another fun idea is to drizzle a bit of warm caramel or pineapple glaze over the cookies just before serving for added indulgence. These cookies also make whimsical cupcake toppers or favors when dressed up with a little edible gold leaf!

Make Ahead and Storage

Storing Leftovers

After enjoying your batch, place leftover Pineapple Upside Down Cookies in an airtight container at room temperature. They stay fresh and delicious for about 3 to 4 days, maintaining their soft texture and fruity flavor without drying out.

Freezing

If you want to save some for later, wrap each cookie tightly in plastic wrap and freeze them inside a freezer-safe container. They hold up well for up to 2 months. Just thaw overnight in the fridge before reheating.

Reheating

Reheat your cookies gently in a 300°F oven for about 5 minutes to refresh their softness and melt the caramel just a bit. Avoid microwaving, as it can make the texture rubbery and uneven.

FAQs

Can I use fresh pineapple instead of canned rings?

Absolutely! If you have fresh pineapple, slice it into thin rounds and dry them well before using. Keep in mind fresh pineapple has more moisture, so pat them dry thoroughly to avoid soggy cookies.

Do I need to use cream of tartar for this recipe?

Cream of tartar helps stabilize the cookies and provides a subtle tang, but if you don’t have it, you can substitute with an equal amount of lemon juice or white vinegar. Just keep the quantity small to maintain the balance.

Can I make these gluten-free?

Yes! Substitute the all-purpose flour with a 1-to-1 gluten-free baking flour blend. Be sure to check that the blend includes xanthan gum for the best texture and binding.

What’s the best way to prevent sticking when flipping the pan?

Greasing the muffin pan well and using parchment paper under the cookie sheet you flip the pan onto helps prevent sticking. Also, flipping the pan while it’s still warm makes the cookies release more easily.

How long do Pineapple Upside Down Cookies keep their texture?

These cookies are best enjoyed within a few days of baking when they’re still soft and moist. After that, they might start to dry out, but reheating gently can help bring back some of the original softness.

Final Thoughts

Making Pineapple Upside Down Cookies is more than just baking; it’s about sharing joy and tropical flavors with those around you. The blend of caramelized sugar, juicy pineapple, and sweet cherries on a tender cookie base is simply irresistible. Whether for a casual snack, a special occasion, or a sweet surprise, these cookies are sure to become a beloved staple in your kitchen. So gather your ingredients, preheat your oven, and get ready to fall in love with the magic of Pineapple Upside Down Cookies.

Pineapple Upside Down Cookies Recipe

★★★★★

4.7 from 29 reviews

Author: Harry
Total Time: 30 minutes
Yield: 12 cookies 1x
Diet: Vegetarian

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Description

These Pineapple Upside Down Cookies combine the classic tropical flavors of pineapple and maraschino cherries with a buttery, soft cookie base. Featuring a delightful brown sugar butter topping, these cookies are baked upside down for a visually stunning presentation and a rich, caramelized taste.

Instructions

Pan Preparations: Preheat your oven to 350°F (175°C). In a smaller mixing bowl, combine 6 tablespoons of melted butter with 1 cup of brown sugar and mix until smooth. Drain the pineapple rings and maraschino cherries thoroughly to prevent excess moisture.
Arrange Toppings: Place about 1 tablespoon of the brown sugar butter mixture into each well of your muffin tin. Press one pineapple ring into the mixture, then place one maraschino cherry in the center of the pineapple ring. Stagger the positions of the toppings to allow cookies room to spread without touching.
Make Cookie Dough: In a mixing bowl, cream together softened butter and granulated sugar until light and fluffy, scraping the sides as needed. Add the egg and vanilla extract, continuing to cream for 2 to 3 minutes until well combined.
Incorporate Wet Ingredients: Gradually add the vegetable oil and powdered sugar to the butter mixture, beating until pale yellow and thoroughly combined.
Add Dry Ingredients: Sift together the all-purpose flour, baking soda, and cream of tartar. Gradually add these dry ingredients to the wet mixture, mixing until fully incorporated into a cookie dough.
Shape Cookies: Using a #24 cookie scoop, portion the dough into balls. Flatten each ball with your palm to about 3 inches in diameter.
Assemble Cookies: Place each flattened cookie dough piece on top of the pineapple ring and cherry in the muffin tin wells. Carefully tuck and press the dough into the sides of each well, sealing the edges to encase the fruit and sugar mixture.
Bake: Bake the cookies at 350°F for 8 to 10 minutes, or until the edges are lightly golden and the centers are no longer glossy.
Invert Cookies: Remove the muffin tin from the oven and immediately invert the pan onto a parchment-lined baking sheet. The cookies will fall out, revealing the classic pineapple upside down topping on top.
Cool and Serve: Allow the cookies to cool completely before serving to let the caramelized topping set for the best flavor and texture experience.

Notes

Make sure to drain pineapple rings and maraschino cherries very well to prevent soggy cookies.
Use a non-stick muffin tin or lightly grease the pan to help cookies release easily after baking.
Stagger cookie placement in the pan to avoid merging during baking.
If desired, substitute vegetable oil with melted coconut oil for a subtle tropical flavor twist.
Store cooled cookies in an airtight container at room temperature for up to 4 days.

Prep Time: 20 minutes
Cook Time: 10 minutes
Category: Dessert, Cookies
Method: Baking
Cuisine: American