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Pineapple Upside-Down Sugar Cookies

Olivia

By Olivia

Mar 9, 2026

15 min prep
30 min cook
12 servings
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Pineapple Upside-Down Sugar Cookies

Welcome to a delightful twist on a beloved classic! These Pineapple Upside-Down Sugar Cookies marry the soft, buttery goodness of a sugar cookie with the tropical sweetness of caramelized pineapple and cherries. Each bite is a melt-in-your-mouth experience that will transport you to a sun-soaked beach, even if you're just enjoying them at home.

Perfectly golden and beautifully topped, these cookies are not just a treat for the taste buds but also a feast for the eyes. Whether you're hosting a gathering or simply treating yourself, these cookies are sure to impress!

Why You'll Love This Recipe

  • A Tropical Twist: Enjoy the bright, refreshing flavor of pineapple paired with the sweetness of cherries.
  • Soft and Buttery: The sugar cookies are soft, tender, and perfectly chewy, making them hard to resist.
  • Easy to Make: With simple ingredients and straightforward steps, these cookies come together quickly and effortlessly.
  • Perfect for Any Occasion: Whether it's a birthday party or a casual afternoon snack, these cookies fit right in!

About the Ingredients

All-Purpose Flour

The foundation of any great cookie, all-purpose flour provides the structure needed for soft, chewy cookies.

Granulated Sugar

This sweetener not only adds sweetness but also helps create a light and fluffy texture in the dough.

Unsalted Butter

Butter brings richness and a delightful flavor to the cookies, ensuring they melt in your mouth.

Large Egg

An essential binding agent, the egg helps hold the dough together while adding moisture and richness.

Baking Powder

This leavening agent gives the cookies a light, airy texture, making them a joy to bite into.

Canned Pineapple Rings

These provide a juicy, tangy flavor that contrasts beautifully with the sweetness of the cookie and cherries.

Brown Sugar

Adding a hint of caramel flavor, brown sugar enhances the overall sweetness while keeping the cookies moist.

Maraschino Cherries

These bright red cherries not only add a pop of color but also a sweet, nostalgic taste that ties the cookie together.

Tips & Tricks

Chill the Dough

For extra fluffy cookies, chill the dough in the fridge for 30 minutes before baking.

Use Fresh Pineapple

If you prefer, you can use fresh pineapple instead of canned for an even fresher taste.

Don't Overbake

Keep a close eye on the cookies; they should be lightly golden and soft in the center when done.

Experiment with Toppings

Feel free to add nuts or coconut for an even more tropical flavor!

Pro Tips

  • Use Room Temperature Ingredients: Ensure your butter is softened to create a creamy texture when mixed with sugar.
  • Measure Flour Properly: Spoon flour into your measuring cup and level it off to avoid dense cookies.
  • Press Lightly: When covering the pineapple, press the cookie dough just enough to secure it without flattening.
  • Let Cool Completely: Allow cookies to cool on the tray for a bit to set before transferring them to a wire rack.

Step-by-Step Instructions

Preheat Your Oven

Start by preheating your oven to 350°F (175°C) to ensure even baking.

Prepare the Baking Sheet

Line a baking sheet with parchment paper to prevent sticking and make cleanup a breeze.

Cream Butter and Sugar

In a large bowl, cream together the softened butter and granulated sugar until it’s light and fluffy, creating the perfect base for your cookies.

Combine Ingredients

Add in the egg, followed by the flour, baking powder, and salt. Stir until the dough comes together, forming a soft and pliable mixture.

Top and Bake

Assemble each cookie by placing a spoonful of dough over the pineapple and cherry, then bake for 12–15 minutes until they are beautifully golden and fragrant.

Delicious Variations

Chocolate Chip Delight

Add chocolate chips for a delightful contrast with the pineapple and cherries.

Coconut Macaroon Style

Incorporate shredded coconut into the dough for a tropical coconut flavor.

Spiced Sugar Cookies

Add a pinch of cinnamon or nutmeg to the dough for a warm, spiced flavor that pairs well with the fruit.

How to Store Pineapple Upside-Down Sugar Cookies

Refrigerator

Store in an airtight container for up to a week to keep them fresh and soft.

Freezer

Freeze the uncooked dough for up to three months; just scoop and bake when you’re ready!

Reheating

Warm in the microwave for a few seconds for that just-baked taste, or place in a 300°F oven for a few minutes.

Frequently Asked Questions

Can I use fresh pineapple?

Absolutely! Fresh pineapple adds a delightful texture and flavor to the cookies.

How do I make the cookies thicker?

Chilling the dough can help create thicker cookies; just refrigerate for about 30 minutes before baking.

What can I substitute for the maraschino cherries?

You can use fresh cherries or even blueberries for a different fruit twist!

Can I make these cookies ahead of time?

Yes, you can prepare the dough and freeze it, then bake them fresh when you’re ready to enjoy!

Now that you've discovered this delightful recipe, it’s time to get baking! Treat yourself and your loved ones to these Pineapple Upside-Down Sugar Cookies that are sure to bring a smile to every face. Happy baking!

Pineapple Upside-Down Sugar Cookies

Pineapple Upside-Down Sugar Cookies

Soft sugar cookies topped with caramelized pineapple and cherries for a delicious twist on a classic dessert everyone will love.

15 min
Prep Time
30 min
Cook Time
12
Servings
220 kcal
Calories

Ingredients

Instructions

  1. 1 Preheat oven to 350°F (175°C).
  2. 2 Line a baking sheet with parchment paper.
  3. 3 In a large bowl, cream the softened butter and granulated sugar until light and fluffy.
  4. 4 Mix in the egg until fully combined.
  5. 5 Add flour, baking powder, and salt. Stir until the dough forms and pulls together.
  6. 6 Sprinkle a spoonful of brown sugar onto the center of each pineapple half.
  7. 7 Place a maraschino cherry in the middle of each piece.
  8. 8 Set the pineapple pieces cherry-side down on the baking sheet.
  9. 9 Scoop cookie dough over each pineapple piece, gently pressing to cover the back.
  10. 10 Bake for 12–15 minutes, or until the cookies are lightly golden around the edges.
  11. 11 Allow them to cool for at least 10 minutes before lifting gently from the tray.
  12. 12 Serve warm or at room temperature.

Chef's Note

Use room-temperature butter for the best cookie texture. If the cookies stick, let them cool longer before lifting. Make the cookies smaller by cutting pineapple rings into thirds. Perfect for summer gatherings or holiday trays.

Servings: 12

Cuisine: American

Course: Dessert

Nutrition (per serving): 2gg protein