Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite

Crispy Pineapple Upside Down Sugar Cookies are a family favorite dessert that’s better than takeout. After making these many times, I discovered the trick to perfectly crispy cookies every time. The caramelized pineapple topping is the star of this show, with its golden color and irresistible sweetness. Keep reading for my best tips. If you love recipes like this, you’ll also enjoy Crispy Oven Baked Sweet Potato Fries and Creamy Crack Chicken Pasta That's Better Than Takeout.

What You'll Need for Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite

Choosing the right ingredients makes a big difference, but this recipe is forgiving enough to work with what you have.

• 1 cup unsalted butter, softened
• 1 cup granulated sugar
• 1 large egg
• 2 teaspoons vanilla extract
• 2 and 1/2 cups all-purpose flour
• 1 teaspoon baking powder
• 1/2 teaspoon salt
• 1 (20 oz) can pineapple chunks in juice, drained
• 1/2 cup packed light brown sugar
• 1/4 cup unsalted butter, melted
• Optional: Maraschino cherries, optional

How to Make Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite

1. Step 1: Preheat oven to 375°F (190°C). Grease a 9×13-inch baking dish or line with parchment paper.
2. Step 2: In a large bowl, cream together butter and granulated sugar until light and fluffy. Beat in egg and vanilla extract.
3. Step 3: In another bowl, whisk together flour, baking powder, and salt. Gradually add dry ingredients to wet ingredients, mixing just until combined.
4. Step 4: Spread pineapple chunks evenly in the prepared baking dish. Sprinkle brown sugar over pineapple. Drizzle melted butter over brown sugar.
5. Step 5: Drop rounded tablespoons of dough evenly over pineapple mixture. Place a maraschino cherry in the center of each dough ball, if desired.
6. Step 6: Bake for 25-30 minutes or until edges are golden brown and center is set. Let cool for 10 minutes before inverting onto a serving platter.

Storing & Reheating Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite

Short-Term Storage

Store in an airtight container in the fridge. Store in an airtight container at room temperature for up to 5 days. Make-ahead tip: Prepare the dough ahead of time and store in the refrigerator for up to 2 days.

Freezing Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite

Freeze for up to 3 months. Thaw at room temperature before serving.

How to Reheat Without Drying It Out

Oven: Reheat in a 350°F (175°C) oven for 10-15 minutes. Microwave: Reheat in the microwave for 15-20 seconds.

Recipe Notes

• Chef tip: For a more caramelized topping, sprinkle a little extra brown sugar on the pineapple before baking.
• Best substitution: Substitute canned mandarin oranges for pineapple for a different flavor twist.
• Make-ahead: Prepare the dough ahead of time and store in the refrigerator for up to 2 days. Bake as directed when ready to serve.
• Scaling: This recipe can be halved to make a smaller batch, or doubled to serve a crowd.
• Troubleshooting: If the cookies are browning too quickly, tent the pan with aluminum foil and continue baking.

Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite

⏱

Prep

20 minutes

🍳

Cook

30 minutes

⏳

Total

50 minutes

🍽

Serves

18 cookies

🥗

Diet

Gluten-free (use gluten-free flour)

Ingredients

Main Ingredients

• 1 cup unsalted butter, softened
• 1 cup granulated sugar
• 1 large egg
• 2 teaspoons vanilla extract
• 2 and 1/2 cups all-purpose flour
• 1 teaspoon baking powder
• 1/2 teaspoon salt

Seasonings

• 1 (20 oz) can pineapple chunks in juice, drained
• 1/2 cup packed light brown sugar
• 1/4 cup unsalted butter, melted

Optional Toppings

• Maraschino cherries, optional

Instructions

1. Step 1: Preheat oven to 375°F (190°C). Grease a 9×13-inch baking dish or line with parchment paper.
2. Step 2: In a large bowl, cream together butter and granulated sugar until light and fluffy. Beat in egg and vanilla extract.
3. Step 3: In another bowl, whisk together flour, baking powder, and salt. Gradually add dry ingredients to wet ingredients, mixing just until combined.
4. Step 4: Spread pineapple chunks evenly in the prepared baking dish. Sprinkle brown sugar over pineapple. Drizzle melted butter over brown sugar.
5. Step 5: Drop rounded tablespoons of dough evenly over pineapple mixture. Place a maraschino cherry in the center of each dough ball, if desired.
6. Step 6: Bake for 25-30 minutes or until edges are golden brown and center is set. Let cool for 10 minutes before inverting onto a serving platter.

Notes

• Chef tip: For a more caramelized topping, sprinkle a little extra brown sugar on the pineapple before baking.
• Best substitution: Substitute canned mandarin oranges for pineapple for a different flavor twist.
• Make-ahead: Prepare the dough ahead of time and store in the refrigerator for up to 2 days. Bake as directed when ready to serve.
• Scaling: This recipe can be halved to make a smaller batch, or doubled to serve a crowd.
• Troubleshooting: If the cookies are browning too quickly, tent the pan with aluminum foil and continue baking.

Storage

• Fridge: Store in an airtight container at room temperature for up to 5 days.
• Freezer: Freeze for up to 3 months. Thaw at room temperature before serving.
• Oven reheat: Reheat in a 350°F (175°C) oven for 10-15 minutes.
• Microwave reheat: Reheat in the microwave for 15-20 seconds.
• Make ahead: Prepare the dough ahead of time and store in the refrigerator for up to 2 days.

Nutrition Per Serving

• Calories: 150
• Protein: 1g
• Fat: 7g
• Carbs: 20g
• Fiber: 0g
• Sugar: 12g
• Sodium: 80mg
• Cholesterol: 25mg
• Sat. Fat: 4g

Nutritional values are estimates only. Actual values may vary by brand and portion size.

Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite FAQs

A Warm Final Note

I can’t wait for you to try Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite and see how effortlessly it comes together. When you make it, pop back here and leave a rating or share how it turned out — I love hearing from you!