Introduction

Pineapple Upside-Down Cookies are a delightful twist on the classic dessert, combining tender, buttery cookies with a caramelized, fruity topping. These small treats offer a burst of tropical flavor with every bite, perfect for sharing or enjoying as a sweet snack.

The image shows a close-up of three round pineapple upside-down mini cakes stacked on top of each other on a white marbled surface. Each small cake has a golden yellow pineapple ring on top with a bright red cherry in the center. The pineapple rings have a glossy, slightly sticky texture, and the cherry is shiny and smooth. The cakes themselves appear moist with a light golden brown color visible around the edges. The overall look is fresh and colorful, with the pineapple’s yellow contrasting nicely with the red cherries. 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 your oven to 350°F (175°C). Line a baking sheet with parchment paper.
Step 2: In a large bowl, cream together the softened unsalted butter and granulated sugar until light and fluffy.
Step 3: Beat in the egg and vanilla extract until well combined.
Step 4: In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add this to the wet mixture, mixing until just combined.
Step 5: In a small bowl, mix the brown sugar with melted butter to create a sticky base.
Step 6: Drop small spoonfuls of the brown sugar mixture onto the prepared baking sheet, spacing them evenly.
Step 7: Top each brown sugar dollop with a piece of pineapple and a halved maraschino cherry.
Step 8: Using a cookie scoop or spoons, gently drop cookie dough on top of the pineapple pieces, fully covering the fruit.
Step 9: Bake for 12–15 minutes, or until the cookies are golden brown around the edges.
Step 10: Allow cookies to cool on the baking sheet for 5 minutes, then carefully invert them onto a cooling rack so the caramelized pineapple is on top.

Tips & Variations

Substitute brown sugar for granulated sugar to enhance the caramel flavor throughout the cookie.
Use fresh pineapple tidbits instead of canned for a fresher taste; just make sure pieces are small and dry.
Replace maraschino cherries with dried cranberries or fresh cherries for a different fruity twist.
For an egg-free version, use a flax egg (1 tbsp ground flaxseed mixed with 3 tbsp water) instead of a large egg.
Try adding a pinch of cinnamon or nutmeg to the dough for extra warmth and depth of flavor.

Storage

Store the cookies in an airtight container at room temperature for up to 3 days. For longer storage, keep them refrigerated for up to a week. To reheat, warm gently in a microwave for 10-15 seconds to restore softness and bring out the caramel flavor.

How to Serve

The image shows a stack of three round pineapple rings, each bright yellow with a slightly shiny, juicy texture. On top of each pineapple ring, in the center, there is a small red strawberry slice with visible seeds and a fresh, moist look. The stack is placed on a smooth white plate with a simple edge. The background features a white marbled texture, giving a clean and fresh setting. photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I make these cookies gluten-free?

Yes, you can substitute the all-purpose flour with a 1:1 gluten-free flour blend. Just be sure the blend contains xanthan gum or another binder to keep the cookies from crumbling.

Why do the cookies need to be inverted after baking?

Inverting the cookies while they’re still warm allows the caramelized brown sugar and pineapple topping to be on top, creating the signature upside-down effect and enhancing flavor and presentation.

Pineapple Upside-Down Cookies Recipe

Print Recipe

★★★★★

4.6 from 126 reviews

These Pineapple Upside-Down Cookies combine the tropical sweetness of pineapple and maraschino cherries with a rich, buttery cookie base. Featuring a caramelized brown sugar topping that gives the cookies a delightful upside-down effect, this recipe is perfect for a tropical twist on classic cookies that are tender, flavorful, and visually appealing.

Author: Isabella
Prep Time: 15 minutes
Cook Time: 20 minutes
Total Time: 35 minutes
Yield: 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

Caramelized Topping

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

Instructions

Prepare the caramelized base: In a small bowl, combine the brown sugar and melted butter until well blended. Press this mixture evenly into the bottom of your cookie baking pan or muffin tins to form the caramelized base.
Arrange the fruit: Place cut pineapple pieces evenly over the brown sugar mixture. Add halved maraschino cherries atop the pineapple to add color and a burst of sweetness.
Make the cookie dough: In a mixing bowl, cream the softened unsalted butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until fully incorporated.
Combine dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, and salt to evenly distribute the leavening agents and salt.
Mix dry into wet: Gradually add the dry ingredients to the wet batter, mixing until just combined to avoid overworking the dough, which can make the cookies tough.
Assemble and bake: Gently drop or spoon the cookie dough over the fruit and caramel base, spreading lightly to cover. Bake the cookies in a preheated oven at 350°F (175°C) for 18-22 minutes or until the cookies are golden and set.
Cool and invert: Allow the cookies to cool for about 10 minutes. Carefully invert the pan onto a cooling rack so the caramelized pineapple and cherry topping are exposed on top, revealing the classic upside-down look.
Serve and enjoy: Let the cookies cool completely before serving. These cookies pair beautifully with a cup of tea or as a sweet treat any time of the day.

Notes

For a gluten-free version, substitute the all-purpose flour with a 1:1 gluten-free baking flour.
If allergic to eggs, replace the egg with a flax egg (1 tbsp ground flaxseed mixed with 3 tbsp water, let sit for 5 minutes to thicken).
Fresh pineapple can be used instead of canned, but cut it into small pieces to ensure even baking.
Brown sugar in the topping creates the signature caramelized effect; do not substitute with white sugar.
Use salted butter but reduce added salt in the dough to ⅛ tsp to avoid over-salting.
Handle the inversion step gently to prevent the cookies from breaking apart.

Keywords: pineapple cookies, upside-down cookies, tropical cookies, caramelized cookies, pineapple dessert