Pineapple Upside Down Sugar Cookies – Quick and Easy Dessert Idea

As a kid, I loved sneaking into the kitchen to watch my grandmother caramelize pineapple for her famous cakes. That nostalgic charm inspired me to create pineapple upside down sugar cookies—an old fashioned pineapple treat you can enjoy without the fuss of a whole cake. These cookies are quick, easy, and family-friendly, perfect for busy weeknights or special occasions. Try this classic pineapple upside down sugar cookies recipe for a sweet, memorable treat.

Why You’ll Love This Recipe

If you love nostalgic desserts with a tropical twist, this pineapple upside down sugar cookies recipe is made for you. These cookies combine the buttery, soft texture of a classic sugar cookie with the caramelized sweetness of pineapple on top, giving you an old fashioned pineapple upside down sugar cookies experience in every bite. Perfect for family gatherings, busy weeknights, or special occasions, this recipe is easy, quick, and customizable. Whether you want to try the classic pineapple upside down sugar cookies recipe or experiment with new variations, these cookies deliver on flavor, presentation, and comfort. Kids and adults alike will enjoy these sweet treats, and they’re simple enough to make any day of the week. With minimal prep, balanced ingredients, and the nostalgic charm of old fashioned pineapple upside down sugar cookies, you’ll find yourself coming back to this recipe again and again.

Ingredients for This Recipe

Every ingredient in this pineapple upside down sugar cookies recipe plays a key role in creating the perfect balance of sweetness, texture, and flavor. The all-purpose flour, baking powder, and baking soda give the cookies structure and a light, tender crumb, while the butter and vegetable oil keep them soft and moist. Granulated sugar adds sweetness to the dough, complemented by the vanilla for a warm, aromatic flavor. The egg binds everything together and contributes to the cookie’s rich, old fashioned pineapple upside down sugar cookies taste.

The pineapple topping is what truly makes this recipe special. Brown sugar and melted butter caramelize beautifully in the oven, while pineapple rings or chunks provide that tropical, juicy burst of flavor. Maraschino cherries add a fun, colorful touch and enhance the nostalgic charm of old fashioned pineapple upside down sugar cookies. Each cookie is a perfect combination of buttery sweetness and fruity caramel goodness.

🛒 Ingredients (for 12–16 cookies):

For the Cookie Dough:
2 ½ cups all-purpose flour
1 teaspoon baking powder
½ teaspoon baking soda
¼ teaspoon salt
½ cup (1 stick) unsalted butter, softened
½ cup vegetable oil
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract

For the Pineapple Topping:
½ cup brown sugar, packed
2 tablespoons unsalted butter, melted
8–10 small pineapple rings or chopped pineapple chunks
12 maraschino cherries (optional, for garnish)

How to Make This Recipe

Making pineapple upside down sugar cookies is easier than it looks, and each step highlights the sweet, nostalgic charm of this old fashioned pineapple dessert. Start by preparing the pineapple topping, which is the signature part of these cookies. Brown sugar and melted butter combine to create a caramel base, while pineapple rings or chunks and maraschino cherries add tropical sweetness and a pop of color. This topping will sit perfectly under the cookie dough as it bakes.

Next, the cookie dough itself is simple but essential for the classic pineapple upside down sugar cookies texture. Softened butter, vegetable oil, sugar, egg, and vanilla are creamed together to create a rich, tender base. Flour, baking powder, baking soda, and salt are added gradually to maintain a soft crumb. Once the dough is ready, scoop it onto the prepared pineapple topping and gently flatten. Baking brings the cookies together, caramelizing the pineapple while leaving the sugar cookie soft and golden.

🛒 Steps:

Preheat oven to 350°F (175°C).
Mix brown sugar and melted butter; place a teaspoon of mixture on a lined baking sheet.
Add pineapple pieces and optional maraschino cherry on top of each sugar mixture.
In a bowl, cream butter, vegetable oil, and sugar until smooth.
Beat in egg and vanilla extract until combined.
Gradually add flour, baking powder, baking soda, and salt; mix until dough forms.
Scoop dough (1 tablespoon per cookie) and gently press on top of pineapple topping.
Flatten slightly with hand or spoon.
Bake 12–15 minutes until edges are lightly golden.
Cool 5 minutes on pan, then transfer to wire rack.
Serve warm or store in an airtight container for up to 4 days.

Expert Cooking Tips

Creating the perfect pineapple upside down sugar cookies is all about balancing the soft, buttery sugar cookie with the caramelized pineapple topping. The cookie dough ingredients—flour, butter, oil, sugar, egg, and vanilla—work together to produce a tender base that complements the sweet, juicy pineapple. The brown sugar and butter topping caramelizes in the oven, enhancing the flavor of the pineapple pieces. Using fresh or canned pineapple affects moisture levels, so adjusting the dough slightly can ensure the classic pineapple upside down sugar cookies texture remains soft and chewy.

For the best results, choose ripe, sweet pineapple to maximize natural flavor and avoid overly wet cookies. Pressing the cookie dough lightly over the topping ensures it sticks without sliding off. Maraschino cherries are optional, but they enhance the nostalgic appearance and appeal of old fashioned pineapple upside down sugar cookies. Following these tips will make every batch consistent, flavorful, and visually appealing.

💡 Expert Tips:

Use fresh or well-drained canned pineapple for best results.
Slightly underbake cookies for a soft, chewy texture.
Press dough gently onto pineapple topping to prevent sliding.
Use a teaspoon of brown sugar and butter per cookie for caramelized flavor.
Add a cherry on top for classic old fashioned pineapple upside down sugar cookies appearance.
Store cookies in an airtight container to maintain freshness.
Experiment with cookie size for mini or larger treats without changing baking time significantly.

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Pineapple upside down sugar cookies are the perfect combination of buttery sugar cookies and sweet, caramelized pineapple, bringing a nostalgic old fashioned pineapple upside down sugar cookies flavor to every bite. Easy to make, customizable, and family-friendly, this recipe works for busy weeknights, special occasions, or a fun baking project with kids. Whether you follow the classic pineapple upside down sugar cookies recipe or add your own twist, these cookies are sure to delight with every soft, fruity, and caramelized bite.

Pineapple Upside Down Sugar Cookies

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• Author: Savannah
• Total Time: ~45 minutes
• Yield: 12–16 cookies 1x
• Diet: Vegetarian

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Description

Soft, buttery sugar cookies topped with caramelized pineapple and a cherry, inspired by the classic pineapple upside down cake. These cookies are easy to make, perfect for parties, and bring a nostalgic old fashioned flavor to every bite.

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Ingredients

Scale 1x2x3x

🛒 Ingredients (for 12–16 cookies):

For the Cookie Dough:

• 2 ½ cups all-purpose flour

• 1 teaspoon baking powder

• ½ teaspoon baking soda

• ¼ teaspoon salt

• ½ cup (1 stick) unsalted butter, softened

• ½ cup vegetable oil

• 1 cup granulated sugar

• 1 large egg

• 1 teaspoon vanilla extract

For the Pineapple Topping:

• ½ cup brown sugar, packed

• 2 tablespoons unsalted butter, melted

• 8–10 small pineapple rings or chopped pineapple chunks

• 12 maraschino cherries (optional, for garnish)

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Instructions

📝 Instructions:

Step 1: Prep Pineapple Topping

1. Preheat oven to 350°F (175°C).

2. Mix brown sugar and melted butter in a small bowl.

3. Line a baking sheet with parchment paper. Spoon a teaspoon of the brown sugar mixture onto each cookie space. Top each with a small pineapple piece and optionally a cherry.

Step 2: Make Cookie Dough

1. In a medium bowl, whisk flour, baking powder, baking soda, and salt.

2. In a large bowl, cream butter, oil, and sugar until smooth. Beat in egg and vanilla.

3. Gradually add dry ingredients, mixing until dough forms.

Step 3: Assemble Cookies

1. Scoop dough (about 1 tablespoon each) and gently press on top of the pineapple topping.

2. Slightly flatten each cookie with your hand or a spoon.

Step 4: Bake

1. Bake for 12–15 minutes, or until edges are lightly golden.

2. Remove from oven and let cool on the pan for 5 minutes, then carefully transfer to a wire rack.

Step 5: Serve & Enjoy

1. Serve warm or at room temperature. Cookies can be stored in an airtight container for up to 4 days.

Notes

• Chewy or Soft: Slightly underbake for softer cookies.

• Mini Version: Use smaller dough portions for bite-sized treats.

• Make Ahead: Dough can be refrigerated for 24 hours before baking.

• Prep Time: 20 minutes
• Cook Time: 12–15 minutes
• Category: Dessert / Cookie
• Method: Baked / Topped / Decorated
• Cuisine: American