Dessert

Pineapple Upside Down Sugar Cookies Recipe

ByJulian Dempsey February 4, 2026February 4, 2026

Introduction

These Pineapple Upside Down Sugar Cookies combine the classic flavors of the beloved pineapple upside down cake with a soft, buttery cookie base. Topped with caramelized brown sugar, juicy pineapple slices, and bright maraschino cherries, they make a delightful treat perfect for any occasion.

Four small upside-down cakes sit on a white plate, each cake having three visible layers: the bottom layer is a golden brown cake base with a slightly crumbly texture; the middle layer is a glossy, caramelized syrup coating that glistens under the light; the top layer is a bright yellow pineapple ring with a shiny surface, and in the center of each pineapple ring is a small, round red cherry that adds a pop of color. The cakes are slightly spaced apart on a white marbled surface, with small drips of syrup scattered around them. photo taken with an iphone --ar 4:5 --v 7

Ingredients

1 cup butter (room temperature)
1 1/2 cups granulated sugar
2 eggs
2 tsp. vanilla extract
1/2 cup sour cream
3 cups all-purpose flour
1 tsp. baking powder
1 tsp. cornstarch
1/2 tsp. salt
13 canned pineapple slices
13 maraschino cherries
1/2 cup butter (melted)
1 cup light brown sugar (packed)

Instructions

Step 1: Preheat your oven to 350 degrees Fahrenheit and prepare a USA pan mini round cake pan by setting it aside.
Step 2: In a large mixing bowl, beat together the room temperature butter and granulated sugar until the mixture is light and fluffy.
Step 3: Add in the eggs, vanilla extract, and sour cream, mixing until fully combined.
Step 4: Gradually add the flour, baking powder, cornstarch, and salt. Mix just until the dough comes together, then set it aside.
Step 5: In a separate bowl, combine the melted butter and packed brown sugar, stirring until blended.
Step 6: Spoon about one tablespoon of the brown sugar mixture into the bottom of each pan cavity, spreading it evenly to cover the surface.
Step 7: Place one pineapple slice over the brown sugar in each cavity, then position a maraschino cherry in the center of each pineapple slice.
Step 8: Using a 3-tablespoon cookie scoop, drop cookie dough over each pineapple slice. Flatten gently with an offset spatula to cover evenly.
Step 9: Bake for 25 minutes or until the edges turn golden brown and the brown sugar mixture is bubbling along the sides.
Step 10: Allow the cookies to cool for 10 minutes in the pan, then carefully invert them onto wax paper to catch any spilled brown sugar. If a pineapple slice sticks to the pan, reposition it on the cookie while warm.
Step 11: Let the cookies cool completely before serving. Store in an airtight container and enjoy within 2 to 3 days for the best flavor and texture.

Tips & Variations

For a tropical twist, sprinkle shredded coconut over the brown sugar before adding the pineapple slice.
Use fresh pineapple slices if available, but reduce baking time slightly as they contain more moisture.
Swap maraschino cherries for glace cherries or even pineapple chunks for a different look and flavor.
Make mini versions by using smaller cookie scoops and adjusting baking time accordingly.

Storage

Store the cookies in an airtight container at room temperature for up to 3 days. To maintain their soft texture, avoid refrigerating as it may dry them out. Reheat gently in a microwave for a few seconds if desired to bring back their fresh-baked warmth.

How to Serve

The image shows four small pineapple upside-down cakes placed on a white marbled surface. Each cake has two clear layers: the bottom layer is a golden-brown, moist and textured cake base, while the top layer features a bright yellow, juicy pineapple ring with a glossy sheen. In the center of each pineapple ring sits a shiny red cherry, creating a vibrant color contrast. Some syrup glistens around the edges and drips slightly onto the surface, adding a sticky, glossy effect. The cakes are arranged closely but not touching each other. 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 slices can be used but they contain more moisture, so keep an eye on the baking time and reduce it slightly to prevent sogginess.

What if I don’t have a USA pan mini round cake pan?

You can use a mini muffin pan or a similar small baking pan. Adjust the amount of brown sugar mixture and cookie dough to fit the size of your pan cavities.