Pineapple Upside Down Sugar Cookies: A Delicious Twist on a Classic

By lbc14
October 25, 2026

How to make Pineapple Upside Down Sugar Cookies

Ingredients:

  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 cups all-purpose flour
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1 cup crushed pineapple, drained
  • 1/2 cup brown sugar
  • 12 maraschino cherries, drained

Directions:

  1. Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
  2. In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
  3. Add in the egg and vanilla extract, and mix well until combined.
  4. In another bowl, whisk together the flour, baking soda, and salt until evenly mixed.
  5. Gradually add the dry ingredients to the wet mixture, mixing until everything is just combined.
  6. Fold in the crushed pineapple and brown sugar gently to incorporate them into the batter.
  7. Spread the batter evenly on the prepared baking sheet, smoothing it out to make a nice, even layer.
  8. Place the maraschino cherries on top of the batter, spacing them out as desired.
  9. Bake for 15-20 minutes or until a toothpick inserted into the center comes out clean. Keep an eye on them to avoid overbaking.
  10. Allow to cool before cutting into bars and serving.

Why You’ll Love This Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies take a beloved classic dessert and transform it into a delightful cookie form. The light and chewy cookie base pairs perfectly with the sweetness of the crushed pineapple and the caramel-like flavor of brown sugar. Each bite gives a taste of summer, making them ideal for any occasion, be it a party or a cozy family gathering.

Nutritional Benefits

These cookies offer a few nutritional benefits:

Pineapple Upside Down Sugar Cookies: A Delicious Twist on a Classic
  • Pineapple: Packed with vitamins C and B6, pineapple also has bromelain, which can aid digestion.
  • Butter: Provides essential fats and gives a rich flavor to the cookies.
  • Granulated Sugar: While mainly for sweetness, it provides quick energy.
  • Cherries: Maraschino cherries add a fun color and a small boost of antioxidants.

What to Serve With Pineapple Upside Down Sugar Cookies

These cookies can stand alone, but they pair wonderfully with:

  • A cold glass of milk, which complements their sweetness.
  • Vanilla or coconut ice cream for an extra treat.
  • Fresh fruit salad for a refreshing contrast.
  • A tropical fruit punch for a more festive mood.

How to Store Pineapple Upside Down Sugar Cookies

To keep your cookies fresh, store them in an airtight container at room temperature. They should last for about 3-5 days. If you want to keep them longer, consider freezing them. To freeze, wrap each cookie in plastic wrap and place them in a freezer-safe bag. They can be kept in the freezer for up to 3 months. When you’re ready to enjoy them, simply thaw at room temperature.

Tips and Mistakes to Avoid

  • Don’t skip the draining step: It’s crucial to drain the pineapple well so your cookie batter doesn’t become too wet.
  • Room temperature ingredients: Make sure your butter and egg are at room temperature for easier mixing.
  • Avoid overbaking: Keep an eye on your cookies towards the end of the baking time to prevent them from being dry.
  • Use a measuring cup: For the flour, scoop from the bag with a spoon and gently fill the measuring cup instead of scooping directly, which can compact the flour and lead to dry cookies.

Variations

  • Add nuts: Toasted walnuts or pecans can be mixed into the batter for added texture.
  • Coconut flakes: For a tropical twist, stir in some sweetened coconut flakes.
  • Change the fruit: You can use peaches or cherries instead of pineapple if you prefer. Just ensure they are chopped and drained well.

FAQs

Can I use fresh pineapple instead of canned?

Yes! Fresh pineapple can be used, but make sure it is chopped fine and well-drained before adding to the batter.

Can I make the dough ahead of time?

Absolutely! You can prepare the dough and refrigerate it for up to 24 hours. Just let it come to room temperature before baking.

What if I don’t have maraschino cherries?

If you don’t have maraschino cherries, you can skip them or use dried cherries or pieces of fresh fruit like diced strawberries or kiwi for decoration.

Can these cookies be made gluten-free?

Yes! You can substitute all-purpose flour with a gluten-free flour blend. Just ensure that the blend you choose can be used in baking without altering the final result.

These Pineapple Upside Down Sugar Cookies are not only delicious but also a fun and creative way to enjoy a timeless dessert. With its unique flavors and textures, it is sure to win the hearts of many. Happy baking!

Pineapple Upside Down Sugar Cookies

A delightful twist on a classic dessert, these cookies combine a light, chewy base with sweet crushed pineapple and brown sugar for a refreshing summer treat.
Servings 12 cookies
Prep Time 15 minutes
Cook Time 20 minutes
Total Time 35 minutes

Ingredients
  

Cookie Base

  • 1 cup unsalted butter, softened At room temperature for easier mixing
  • 1 cup granulated sugar For sweetness and quick energy
  • 1 large egg At room temperature
  • 1 teaspoon vanilla extract For flavor
  • 2 cups all-purpose flour Scoop measured for best results
  • 1 teaspoon baking soda For leavening
  • 1/2 teaspoon salt To balance flavors
  • 1 cup crushed pineapple, drained Drain thoroughly to avoid excess moisture
  • 1/2 cup brown sugar For a caramel-like flavor

Topping

  • 12 pieces maraschino cherries, drained For decoration

Instructions
 

Preparation

  • Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
  • In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy.
  • Add the egg and vanilla extract, and mix well until combined.
  • In another bowl, whisk together the flour, baking soda, and salt until evenly mixed.
  • Gradually add the dry ingredients to the wet mixture, mixing until everything is just combined.
  • Fold in the crushed pineapple and brown sugar gently to incorporate them into the batter.

Baking

  • Spread the batter evenly on the prepared baking sheet, smoothing it out to make a nice, even layer.
  • Place the maraschino cherries on top of the batter, spacing them out as desired.
  • Bake for 15-20 minutes or until a toothpick inserted into the center comes out clean. Keep an eye on them to avoid overbaking.
  • Allow to cool before cutting into bars and serving.

Notes

Store in an airtight container at room temperature for 3-5 days. For longer storage, freeze wrapped cookies for up to 3 months. Thaw at room temperature before enjoying.
Calories: 150kcal
Course: Dessert, Snack
Cuisine: American
Keyword: Baking, Pineapple Dessert, Pineapple Upside Down Cookies, Sugar Cookies, Summer Treats

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