Introduction

These Pineapple Upside Down Sugar Cookies combine the classic flavors of a pineapple upside down cake with the ease of a soft sugar cookie. Topped with sweet pineapple slices and maraschino cherries, they make a delightful treat perfect for any occasion.

Pineapple Upside Down Sugar Cookies Recipe - Recipe Image

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. Prepare a USA pan mini round cake pan by setting it aside for later use.
Step 2: In a large mixing bowl, cream together the room temperature butter and granulated sugar until the mixture is light and fluffy.
Step 3: Beat in the eggs, vanilla extract, and sour cream until well combined.
Step 4: Add the all-purpose flour, baking powder, cornstarch, and salt. Mix just until the cookie dough comes together. Then set aside the dough.
Step 5: In a separate bowl, stir the melted butter and brown sugar together until fully combined.
Step 6: Spoon about one tablespoon of the brown sugar mixture into the bottom of each cavity of the cake pan, spreading it evenly to cover the base.
Step 7: Place one pineapple slice on top of the brown sugar in each cavity, then press a maraschino cherry into the center of each pineapple slice.
Step 8: Using a 3-tablespoon cookie scoop, drop a portion of cookie dough on top of the pineapple and cherry in each cavity. Flatten the dough gently with an offset spatula.
Step 9: Bake in the preheated oven for about 25 minutes, or until the edges are golden brown and the brown sugar mixture is bubbling up the sides.
Step 10: Allow the cookies to cool in the pan for 10 minutes. Then carefully invert the pan onto a surface covered with wax paper to release the cookies. If the pineapple slices stick, reposition them onto the cookies.
Step 11: Let the cookies cool completely before serving. Store in an airtight container for best freshness.

Tips & Variations

Use fresh pineapple chunks instead of canned slices for a fresher flavor, but pat them dry to avoid excess moisture.
Swap maraschino cherries with glacé cherries or fresh berries for a different fruity twist.
Make sure to use wax paper when turning out the cookies to catch any sticky brown sugar drips for easy cleanup.
For a dairy-free version, substitute butter with a plant-based alternative and use coconut yogurt instead of sour cream.

Storage

Store these cookies in an airtight container at room temperature for up to 3 days. To reheat, warm them briefly in a microwave or oven to soften the brown sugar topping and bring out the flavors.

How to Serve

Serve this delicious recipe with your favorite sides.

FAQs

Can I make these cookies ahead of time?

Yes, you can prepare the cookie dough and brown sugar topping a day in advance. Keep them refrigerated separately and assemble just before baking for best results.

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

If you don’t have a mini round cake pan, you can try using a standard muffin tin instead. Just be sure to adjust the amount of dough and toppings to fit the size of the cavities.

Pineapple Upside Down Sugar Cookies Recipe

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4.4 from 99 reviews

Delight in these Pineapple Upside Down Sugar Cookies, a creative twist on the classic pineapple upside-down cake. Featuring soft sugar cookie dough baked atop a caramelized brown sugar and butter base, each cookie is topped with a juicy pineapple slice and a bright maraschino cherry. Perfect for a sweet treat that combines tropical flavors with a buttery, tender cookie texture.

Author: Tara
Prep Time: 15 minutes
Cook Time: 25 minutes
Total Time: 40 minutes
Yield: 13 cookies 1x
Category: Dessert
Method: Baking
Cuisine: American

Ingredients

Scale

Cookie Dough

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

Topping

13 canned pineapple slices
13 maraschino cherries
1/2 cup butter (melted)
1 cup light brown sugar (packed)

Instructions

Preheat Oven: Preheat your oven to 350 degrees Fahrenheit. Prepare a USA pan mini round cake pan for baking.
Mix Butter and Sugar: In a large mixing bowl, cream together the room temperature butter and granulated sugar until the mixture is light and fluffy, about 2-3 minutes.
Add Wet Ingredients: Incorporate the eggs, vanilla extract, and sour cream into the butter-sugar mixture. Mix until all ingredients are fully combined and smooth.
Add Dry Ingredients: Gradually add the all-purpose flour, baking powder, cornstarch, and salt. Mix just until the cookie dough comes together. Avoid overmixing to keep cookies tender.
Prepare Brown Sugar Mixture: In a separate bowl, combine the melted butter and packed light brown sugar until well blended.
Assemble Cookie Bases: Spoon about 1 tablespoon of the brown sugar mixture evenly into the bottom of each cavity of the mini round cake pan. Spread to cover the base evenly.
Add Pineapple Slice and Cherry: Place one pineapple slice atop the brown sugar in each cavity, then center a maraschino cherry on top of each pineapple slice.
Top with Cookie Dough: Using a 3 tablespoon cookie scoop, place a scoop of cookie dough over each pineapple and cherry arrangement. Flatten gently with an offset spatula to cover the top evenly.
Bake: Place the pan into the preheated oven and bake for about 25 minutes, or until the cookie edges turn golden brown and the brown sugar mixture is bubbling up the sides.
Cool and Release: Allow the cookies to cool in the pan for 10 minutes. Then carefully invert the pan onto a wax paper-lined surface to release the cookies. Be cautious as the brown sugar may run.
Final Cooling and Storage: Let the cookies cool completely before serving. Store them in an airtight container. These cookies are best enjoyed within 2 to 3 days for optimal freshness.

Notes

Use wax paper when turning out the cookies to catch sticky, melted brown sugar for easy cleanup.
If the pineapple slices stick to the pan when flipping, reposition them carefully back onto the tops of the cookies.
Room temperature butter helps achieve a light, fluffy cookie dough texture for tender cookies.
Do not overmix the dough once dry ingredients are added to avoid tough cookies.
These cookies are best eaten within a few days as the pineapple topping is fresh and juicy.

Keywords: Pineapple upside down cookies, sugar cookies, pineapple cookies, holiday cookies, fruit topped cookies, caramelized brown sugar cookies