Crispy Pineapple Upside Down Sugar Cookies – Better Than Takeout

Crispy Pineapple Upside Down Sugar Cookies that delight every bite. After making these many times, I discovered the trick to the perfect crispy texture. Keep reading for my best tips. If you love recipes like this, you’ll also enjoy Crispy Ravioli Appetizer and Brown Sugar Pineapple Chicken.

What You'll Need for Crispy Pineapple Upside Down Sugar Cookies – Better Than Takeout

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
• 1 teaspoon vanilla extract
• 2 cups all-purpose flour
• 1 teaspoon baking powder
• 1/2 teaspoon salt
• 1 can (20 oz) pineapple chunks, drained
• 1/2 teaspoon ground cinnamon
• 1/4 teaspoon ground nutmeg
• Optional: Vanilla ice cream, for serving

How to Make Crispy Pineapple Upside Down Sugar Cookies – Better Than Takeout

1. Cream Butter and Sugar: In a large bowl, cream together butter and sugar until light and fluffy.
2. Add Egg and Vanilla: Beat in egg and vanilla extract until well combined.
3. Combine Dry Ingredients: In a separate bowl, whisk together flour, baking powder, salt, cinnamon, and nutmeg.
4. Make Dough: Gradually add dry ingredients to wet ingredients, mixing just until combined.
5. Chill Dough: Cover and chill dough for at least 1 hour.
6. Preheat Oven: Preheat oven to 375°F (190°C).
7. Prepare Pineapple: Arrange drained pineapple chunks in the bottom of a 9×13-inch baking dish.
8. Form Cookies: Using a small cookie scoop, drop dough onto pineapple, flattening slightly.
9. Bake: Bake for 18-20 minutes, or until edges are golden brown.
10. Invert: Let cookies cool for 5 minutes, then invert onto a serving platter.

Storing & Reheating Crispy Pineapple Upside Down Sugar Cookies – Better Than Takeout

Short-Term Storage

Store in an airtight container in the fridge. Store leftover cookies in an airtight container in the refrigerator for up to 5 days. Make-ahead tip: Dough can be made ahead and chilled for up to 24 hours.

Freezing Crispy Pineapple Upside Down Sugar Cookies – Better Than Takeout

Freeze baked and cooled cookies 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 5-7 minutes. Microwave: Reheat in the microwave for 15-20 seconds, but be careful not to overheat.

Recipe Notes

• Chef tip: For a shortcut, use a boxed sugar cookie mix and add the spices and pineapple as directed.
• Best substitution: Substitute canned mandarin oranges for a different flavor twist.
• Make-ahead: Baked cookies can be made ahead and frozen for up to 3 months.
• Scaling: This recipe can be halved or doubled depending on your needs.
• Troubleshooting: If cookies are sticking to the pan, try lining the pan with parchment paper before adding the pineapple.

Crispy Pineapple Upside Down Sugar Cookies – Better Than Takeout

⏱

Prep

30 minutes

🍳

Cook

20 minutes

⏳

Total

50 minutes

🍽

Serves

24 cookies

🥗

Diet

Gluten-free option: use gluten-free flour

Ingredients

Main 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 powder
• 1/2 teaspoon salt
• 1 can (20 oz) pineapple chunks, drained

Seasonings

• 1/2 teaspoon ground cinnamon
• 1/4 teaspoon ground nutmeg

Optional Toppings

• Vanilla ice cream, for serving

Instructions

1. Cream Butter and Sugar: In a large bowl, cream together butter and sugar until light and fluffy.
2. Add Egg and Vanilla: Beat in egg and vanilla extract until well combined.
3. Combine Dry Ingredients: In a separate bowl, whisk together flour, baking powder, salt, cinnamon, and nutmeg.
4. Make Dough: Gradually add dry ingredients to wet ingredients, mixing just until combined.
5. Chill Dough: Cover and chill dough for at least 1 hour.
6. Preheat Oven: Preheat oven to 375°F (190°C).
7. Prepare Pineapple: Arrange drained pineapple chunks in the bottom of a 9×13-inch baking dish.
8. Form Cookies: Using a small cookie scoop, drop dough onto pineapple, flattening slightly.
9. Bake: Bake for 18-20 minutes, or until edges are golden brown.
10. Invert: Let cookies cool for 5 minutes, then invert onto a serving platter.

Notes

• Chef tip: For a shortcut, use a boxed sugar cookie mix and add the spices and pineapple as directed.
• Best substitution: Substitute canned mandarin oranges for a different flavor twist.
• Make-ahead: Baked cookies can be made ahead and frozen for up to 3 months.
• Scaling: This recipe can be halved or doubled depending on your needs.
• Troubleshooting: If cookies are sticking to the pan, try lining the pan with parchment paper before adding the pineapple.

Storage

• Fridge: Store leftover cookies in an airtight container in the refrigerator for up to 5 days.
• Freezer: Freeze baked and cooled cookies for up to 3 months. Thaw at room temperature before serving.
• Oven reheat: Reheat in a 350°F (175°C) oven for 5-7 minutes.
• Microwave reheat: Reheat in the microwave for 15-20 seconds, but be careful not to overheat.
• Make ahead: Dough can be made ahead and chilled for up to 24 hours.

Nutrition Per Serving

• Calories: 140
• Protein: 1g
• Fat: 7g
• Carbs: 18g
• Fiber: 0g
• Sugar: 12g
• Sodium: 70mg
• 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 – Better Than Takeout FAQs

A Warm Final Note

I can’t wait for you to try Crispy Pineapple Upside Down Sugar Cookies – Better Than Takeout 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!