Pineapple Upside Down Sugar Cookies

Name: Pineapple Upside Down Sugar Cookies
Prep time: 20 min
Cook time: 25 min
Total time: 45 min
Cuisine: American
Ingredients: 1 cup butter (room temperature); 1 ½ cups granulated sugar; 2 large eggs; 2 teaspoons vanilla extract; ½ cup sour cream; 3 cups all-purpose flour; 1 teaspoon baking powder; 1 teaspoon cornstarch; ½ teaspoon salt; 13 canned pineapple slices; 13 maraschino cherries; ½ cup butter (melted); 1 cup light brown sugar (packed)

By:

Marla Jennings

March 1, 2026

Pineapple Upside Down Sugar Cookies with pineapple and cherries on top

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Pineapple Upside Down Sugar Cookies Recipe

There’s something undeniably nostalgic about the tropical sweetness of pineapple upside-down cake. Now imagine capturing that same vibrant flavor in a soft, chewy cookie—this Pineapple Upside Down Sugar Cookie recipe does just that! Ideal for gatherings, picnics, or satisfying your sweet tooth any day of the week, these cookies bring sunshine to your table. I remember the first time I made these, the way the brown sugar caramelized perfectly with the syrupy pineapple and cherry—pure magic!

Why You’ll Love This Dish

These cookies stand out for several compelling reasons. First and foremost, they bring together the classic flavors of a well-loved dessert in a convenient cookie form. Perfectly sweet yet not overpowering, they strike just the right balance between cake and cookie.

Whether you’re hosting a family brunch or simply want a fun dessert on a weeknight, these treats cater to all occasions. With their whimsical look and delightful taste, they’re sure to become a favorite among kids and adults alike.

“Absolutely delicious! The pineapple and cherry really elevate the flavor. I love how easy they are to make!” — Jamie, satisfied baker

How to Make Pineapple Upside Down Sugar Cookies

This delightful recipe consists of several simple steps that allow you to create impressive cookies without a fuss. Below, you’ll find a brief overview followed by specific ingredients and directions to guide you through the process.

Step-by-step Overview

Preheat your oven and prepare your baking pan.
Make the cookie dough by creaming butter and sugar, then adding eggs and vanilla.
Mix in dry ingredients until just combined.
Prepare the brown sugar mixture and layer it with pineapple and cherries.
Bake to perfection and let cool before serving.

Ingredients

Gather These Items

1 cup butter (room temperature)
1 ½ cups granulated sugar
2 large eggs
2 teaspoons vanilla extract
½ cup sour cream
3 cups all-purpose flour
1 teaspoon baking powder
1 teaspoon cornstarch
½ teaspoon salt
13 canned pineapple slices
13 maraschino cherries
½ cup butter (melted)
1 cup light brown sugar (packed)

Consider using unsalted butter for a more controlled salt level, or opt for gluten-free flour for a gluten-free version of these cookies.

Directions

Step-by-Step Instructions

Preheat your oven to 350 degrees Fahrenheit. Prepare a mini round cake pan by greasing it or lining it with parchment paper.
In a large mixing bowl, cream together the room temperature butter and granulated sugar until the mixture is light and fluffy.
Beat in the eggs one at a time, ensuring they are well incorporated. Then mix in the vanilla extract and sour cream until smooth.
Gradually add the flour, baking powder, cornstarch, and salt. Stir until just combined, being careful not to over-mix.
In a separate bowl, combine the melted butter and brown sugar. Mix until smooth.
Spoon about a tablespoon of the brown sugar mixture into the bottom of each cavity of the pan, spreading it evenly.
Place a pineapple slice atop the brown sugar, then put a cherry in the center of each pineapple slice.
Using a 3-tablespoon cookie scoop, add the cookie dough on top of the pineapple and cherries. Flatten slightly with an offset spatula.
Bake in the preheated oven for around 25 minutes, or until the edges are golden and the brown sugar is bubbling.
Allow to cool for about 10 minutes, then carefully turn the cookies out onto a wax paper-covered surface to cool completely before enjoying.

How to Serve Pineapple Upside Down Sugar Cookies

Best Ways to Enjoy It

These cookies are best served warm but also hold up well at room temperature. For an extra treat, try pairing them with:

A scoop of vanilla ice cream for a delightful sundae twist.
A light drizzle of caramel sauce atop the cookies.
A fresh fruit salad on the side to complement the tropical flavors.

How to Store

Keeping Leftovers Fresh

To ensure your Pineapple Upside Down Sugar Cookies stay delicious, store them in an airtight container at room temperature. They are best consumed within 2 to 3 days for optimal flavor and texture. If you need to keep them longer, you can freeze them wrapped tightly in plastic wrap or a freezer-safe container for up to a month.

Tips to Make

Helpful Cooking Tips

Make sure your butter is at room temperature for better creaming with sugar.
Don’t over-mix the dough after adding the dry ingredients—mix just until combined for soft cookies.
If desired, add a splash of rum extract to the dough for an extra layer of flavor.

Variations

Creative Twists

Feel free to play around with the base recipe. Here are a few fun ideas:

Coconut Pineapple Cookies: Add shredded coconut to the dough for a tropical flair.
Nutty Crunch: Incorporate chopped macadamia nuts or walnuts for added texture.
Vegan Version: Substitute butter with coconut oil and use flax eggs instead of regular eggs to create a vegan-friendly option.

FAQs

Your Questions Answered

Q: Can I use fresh pineapple instead of canned?
A: Yes, fresh pineapple will work! Just make sure to cut it into even slices and cook it slightly to release some juice.

Q: How do I prevent the cookies from sticking to the pan?
A: Greasing the pan thoroughly and using parchment paper will help prevent sticking.

Q: What’s the prep and bake time?
A: The total prep time is about 20 minutes, with a bake time of approximately 25 minutes.

By understanding these basics and following this guide, you’ll be on your way to creating a batch of delightful Pineapple Upside Down Sugar Cookies that will impress everyone at your next gathering!