Introduction

Pineapple upside-down cookies are a delightful twist on a classic cake, offering a perfect balance of buttery cookie and caramelized tropical fruit. These bite-sized treats feature a luscious brown sugar topping with pineapple and cherries for a sweet, colorful surprise.

A pile of round pineapple upside-down cakes is stacked on a white plate, each cake featuring two layers: the top layer is a golden-yellow pineapple ring with a shiny, wet texture and a bright red cherry in the center, creating a vibrant color contrast. The bottom cake layer is a light golden-brown sponge with a soft texture peeking from the sides. The cakes have a slightly glossy sugar coating, giving them a shiny look. The white plate sits on a white marbled surface. photo taken with an iphone --ar 4:5 --v 7

Ingredients

½ cup unsalted butter, softened
¾ cup granulated sugar
1 large egg
1 tsp vanilla extract
1 ¼ cups all-purpose flour
½ tsp baking powder
¼ tsp salt
½ cup brown sugar
2 tbsp melted butter
1 small can pineapple rings, cut into smaller pieces
Maraschino cherries, halved

Instructions

Step 1: Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone baking mat.
Step 2: In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy, using an electric mixer or whisk by hand.
Step 3: Add the egg and vanilla extract, mixing until smooth and slightly glossy.
Step 4: In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add this to the wet ingredients, stirring just until a soft dough forms. Avoid overmixing.
Step 5: In a small bowl, combine the melted butter and brown sugar until smooth.
Step 6: Spoon about 1 teaspoon of the brown sugar mixture onto the lined baking sheet, spacing them apart to allow room for spreading.
Step 7: Place a small piece of pineapple on top of each brown sugar dollop, then add a halved maraschino cherry in the center.
Step 8: Scoop about 1 ½ tablespoons of cookie dough, flatten it slightly, and place it over the fruit and brown sugar mixture. Press gently to seal the edges.
Step 9: Bake for 12-15 minutes, until the cookies are golden around the edges.
Step 10: Let cookies cool on the baking sheet for 5 minutes, then carefully transfer to a wire rack. Once fully cooled, flip them upside-down to reveal the pineapple topping.

Tips & Variations

Use brown sugar instead of granulated sugar for a richer caramel flavor in the cookie dough.
Substitute a flax egg (1 tbsp ground flaxseed + 3 tbsp water) for the egg if you need an egg-free version.
Fresh pineapple finely chopped works well for a fresher taste, just make sure the pieces are small for even baking.
Try dried cranberries instead of maraschino cherries for a tart contrast.

Storage

Store these cookies in an airtight container at room temperature for up to 3 days. For longer storage, refrigerate for up to a week. Reheat briefly in the microwave to soften the caramel topping before serving.

How to Serve

A stack of round pineapple upside-down cakes is shown on a white plate, each cake featuring a bright yellow pineapple ring topped in the center with a glossy red cherry. The top layer clearly shows the juicy texture of the pineapple with light golden brown edges, while the cherry sits shiny and slightly sunken at the center. Below the top cake, a few more cakes are stacked, showing the soft, moist cake layer with a golden-brown color visible between the pineapple slices. The plate sits on a white marbled surface, and the lighting highlights the glossy, wet look of the fruit topping. photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I make the cookie dough ahead of time?

Yes, you can prepare the dough up to 24 hours in advance and keep it refrigerated. Bring it to room temperature before assembling the cookies.

What if I don’t have maraschino cherries?

You can use fresh cherries, dried cranberries, or even a small piece of candied ginger for a different but delicious twist.

Pineapple Upside-Down Cookies Recipe

Print Recipe

★★★★★

4.4 from 463 reviews

These Pineapple Upside-Down Cookies combine the tropical sweetness of pineapple and the rich caramel flavor of brown sugar with a soft, buttery cookie base. Topped with maraschino cherries and a luscious caramelized glaze, these cookies bring a delightful twist to the classic upside-down cake in an easy-to-share bite-sized form, perfect for parties or everyday indulgence.

Author: Bella
Prep Time: 15 minutes
Cook Time: 15 minutes
Total Time: 30 minutes
Yield: About 18 cookies 1x
Category: Dessert
Method: Baking
Cuisine: American

Ingredients

Scale

Cookie Dough

½ cup unsalted butter, softened
¾ cup granulated sugar
1 large egg
1 tsp vanilla extract
1 ¼ cups all-purpose flour
½ tsp baking powder
¼ tsp salt

Topping

½ cup brown sugar
2 tbsp melted butter
1 small can pineapple rings, cut into smaller pieces
Maraschino cherries, halved

Instructions

Prepare the Cookie Dough: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone mat. In a mixing bowl, cream the softened butter and granulated sugar until light and fluffy using an electric mixer or whisk. Then add the egg and vanilla extract, mixing until smooth and glossy. In a separate bowl, whisk together the all-purpose flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, stirring just until a soft dough forms, careful not to overmix.
Prepare the Topping: In a small bowl, combine the melted butter and brown sugar until smooth to create the caramelized base for each cookie. Spoon about a teaspoon of this mixture onto the prepared baking sheet, spacing them apart to allow spreading.
Assemble the Cookies: Place a small piece of pineapple on each brown sugar base, then top with a halved maraschino cherry. Scoop approximately 1 ½ tablespoons of the cookie dough, flatten slightly, and gently place it over the fruit and brown sugar mixture, pressing the edges lightly to seal the topping.
Bake the Cookies: Bake in the preheated oven for 12-15 minutes until cookies are golden around the edges. Remove from the oven and allow them to cool on the baking sheet for 5 minutes to set the topping.
Serve and Enjoy: Once completely cooled, carefully flip the cookies upside down to reveal the pineapple and cherry topping. Serve and enjoy these delightful pineapple upside-down cookies.

Notes

If using salted butter, reduce the added salt in the dough accordingly.
Brown sugar can be swapped for a deeper caramel flavor or omitted for a less sweet version.
For an egg allergy substitute, use a flax egg: 1 tbsp ground flaxseed mixed with 3 tbsp water.
Fresh pineapple can be used; cut into small tidbits for even baking.
Maraschino cherries add color but dried cranberries or fresh cherries can be substituted.
Do not overmix the dough to maintain a soft texture.
Allow cookies to cool before flipping to ensure the caramel topping sets properly.

Keywords: pineapple upside-down cookies, tropical cookies, caramel cookies, fruity cookies, baking, dessert recipe