Introduction

These Pineapple Upside-Down Sugar Cookies offer a delightful twist on a classic dessert, combining the tropical sweetness of pineapple with soft, buttery cookie dough. Perfect for a summer treat or any time you crave a fruity, comforting bite.

A white plate holds a stack of round, pineapple upside-down cakes. Each cake has a golden-brown base layer with a slightly crispy texture, topped with a shiny, bright yellow pineapple slice arranged in a circular pattern showing clear segments. In the center of the pineapple slice, there is a small, caramelized reddish-brown spot that looks sticky and glossy. The cakes are piled loosely, some lying flat and others resting at angles, all with a fresh and moist appearance. The background is a white marbled texture with soft focus. photo taken with an iphone --ar 4:5 --v 7

Ingredients

1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 ½ cups all-purpose flour
1 teaspoon baking powder
½ teaspoon baking soda
½ teaspoon salt
1 can (8 oz) pineapple slices, drained (reserve juice)
¼ cup unsalted butter
½ cup brown sugar, packed
Maraschino cherries (one for each cookie)

Instructions

Step 1: Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper.
Step 2: In a mixing bowl, cream the softened butter and granulated sugar together until light and fluffy, about 3-4 minutes.
Step 3: Add the egg and vanilla extract to the butter mixture, mixing until well blended.
Step 4: In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt.
Step 5: Gradually add the dry ingredients to the creamed butter mixture, stirring gently until just combined.
Step 6: Melt ¼ cup of unsalted butter with the brown sugar in a small saucepan over medium heat, stirring continuously until bubbly and smooth.
Step 7: Spoon about a tablespoon of the butter-sugar mixture into the center of each cookie spot on the prepared baking sheets. Place a pineapple slice on top of each portion.
Step 8: Position a maraschino cherry in the center of each pineapple slice.
Step 9: Scoop about 1 tablespoon of cookie dough and gently spread it over each pineapple slice, covering it slightly while leaving some fruit visible.
Step 10: Bake for 12-15 minutes, or until the cookie edges turn light golden brown.
Step 11: Let cookies cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Tips & Variations

For added texture, try sprinkling chopped pecans or walnuts on top of the pineapple slices before adding the cookie dough.
If you prefer a less sweet cookie, reduce the granulated sugar in the dough to ¾ cup.
Substitute fresh pineapple rings and macerate them with a little brown sugar if canned pineapple isn’t available.

Storage

Store cookies in an airtight container at room temperature for up to 3 days. To keep them fresh longer, refrigerate for up to a week. Reheat gently in a microwave for 10-15 seconds to soften before serving.

How to Serve

The image shows a close-up of several pineapple upside-down cupcakes stacked on a white plate with a dark rim. Each cupcake has one bright yellow pineapple slice on top that is glistening with syrup, creating a shiny texture. In the center of each pineapple ring is a red, glossy maraschino cherry. The cupcakes themselves have a golden brown color, visible around the edges below the pineapple slices. The white plate sits on a surface with a white marbled texture, and the background is softly blurred, placing focus on the cupcakes. photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple rings work well. Slice them thinly and macerate with a bit of brown sugar to mimic the canned pineapple’s sweetness and moisture.

How do I prevent the cookie dough from sliding off the pineapple?

Gently pressing the dough over the pineapple and slightly spreading it helps it adhere better. Also, avoid using too much dough so the pineapple remains visible but still anchored.

Pineapple Upside-Down Sugar Cookies Recipe

Print Recipe

★★★★★

4.9 from 63 reviews

These Pineapple Upside-Down Sugar Cookies blend the classic tropical flavors of pineapple and cherry with a soft, buttery sugar cookie base. Featuring a delightful caramelized brown sugar and butter glaze topped with juicy pineapple slices and maraschino cherries, these cookies are a perfect balance of sweet and tangy. Easy to prepare and baked to golden perfection, they make a charming treat for any occasion.

Author: Cleo
Prep Time: 15 minutes
Cook Time: 15 minutes
Total Time: 30 minutes
Yield: 18–20 cookies 1x
Category: Dessert
Method: Baking
Cuisine: American

Ingredients

Scale

Cookie Dough

1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 ½ cups all-purpose flour
1 teaspoon baking powder
½ teaspoon baking soda
½ teaspoon salt

Topping

1 can (8 oz) pineapple slices, drained (reserve juice)
¼ cup unsalted butter
½ cup brown sugar, packed
Maraschino cherries (one for each cookie)

Instructions

Preheat Oven and Prepare Baking Sheets: Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper to prevent sticking and promote even baking.
Cream Butter and Sugar: In a mixing bowl, cream the softened butter and granulated sugar together using an electric mixer until the mixture becomes light and fluffy, about 3-4 minutes, to incorporate air for a tender cookie.
Add Egg and Vanilla: Beat in the egg and vanilla extract until the mixture is smooth and well combined, ensuring the flavors meld evenly throughout the dough.
Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt to distribute the leavening agents and seasoning evenly.
Mix Dry and Wet Ingredients: Gradually add the dry flour mixture to the creamed butter mixture, stirring gently until just combined to avoid overmixing which can make cookies tough.
Make Brown Sugar Butter Mixture: In a small saucepan over medium heat, melt ¼ cup of unsalted butter with the brown sugar, stirring continuously until the mixture is bubbly and smooth, forming a caramel-like glaze.
Assemble Toppings on Baking Sheets: Spoon about a tablespoon of the warm butter-sugar mixture onto the center of each cookie spot on the prepared baking sheets. Place a pineapple slice on top of each dollop, then position a maraschino cherry in the center of each pineapple slice.
Top with Cookie Dough: Scoop about 1 tablespoon of cookie dough and gently spread it over each pineapple slice, making sure to cover the fruit slightly but leaving some visible for presentation.
Bake the Cookies: Place the baking sheets in the preheated oven and bake for 12-15 minutes, or until the edges of the cookies are lightly golden brown, indicating they are cooked through.
Cool Before Serving: Allow the cookies to cool on the baking sheets for 5 minutes to set, then transfer them to a wire rack to cool completely for best texture and handling.

Notes

Use room temperature butter for easier creaming with sugar.
Do not overmix the dough to keep cookies tender and soft.
Reserve the pineapple juice for another use, such as a cocktail or smoothie.
For a more tropical flavor, consider adding a teaspoon of coconut extract with the vanilla.
Store cookies in an airtight container at room temperature for up to 3 days.

Keywords: pineapple upside-down cookies, sugar cookies, tropical cookies, pineapple cherry cookies, baked cookies, buttery cookies