Easy Pineapple Upside Down Sugar Cookies That Delight Every Bite

Easy Pineapple Upside Down Sugar Cookies are the perfect treat that’s crispy on the outside, soft on the inside, and filled with juicy pineapple. After making these many times, I discovered the trick to the perfect pineapple upside down cookie is to let the pineapple marinate in brown sugar before baking. The result is a cookie that’s better than takeout and a family favorite. Keep reading for my best tips. If you love recipes like this, you’ll also enjoy Easy Baked Ham and Cheese Croissants Recipe and Creamy Lemon Mafaldine Pasta with Broccoli.

What You'll Need for Easy 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 can (20 oz) pineapple chunks
• 1/2 cup unsalted butter, melted
• 1/2 cup granulated sugar
• 1/2 cup brown sugar
• 1 large egg
• 1 tsp vanilla extract
• 1 1/2 cups all-purpose flour
• 1/2 tsp baking powder
• 1/4 tsp salt
• 1 tsp ground cinnamon
• 1/4 tsp ground nutmeg
• Optional: Chopped nuts (optional)
• Optional: Powdered sugar (optional)

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

1. Prepare the pineapple: Drain the pineapple chunks, reserving 1/4 cup of juice. In a small bowl, mix the brown sugar and pineapple juice. Add the pineapple chunks and toss to coat. Let it marinate for 10 minutes.
2. Make the cookie dough: In a large bowl, mix the melted butter, granulated sugar, and brown sugar until well combined. Add the egg and vanilla extract, and mix until smooth. In a separate bowl, combine the flour, baking powder, salt, cinnamon, and nutmeg. Gradually add the dry ingredients to the wet ingredients, mixing just until combined.
3. Assemble the cookies: Preheat the oven to 375°F (190°C). Line a baking sheet with parchment paper or a silicone baking mat. Drop spoonfuls of cookie dough onto the baking sheet, leaving space between each cookie. Top each cookie with a spoonful of the marinated pineapple, including some of the brown sugar mixture. If desired, sprinkle with chopped nuts.
4. Bake the cookies: Bake for 10-12 minutes, or until the edges are golden brown. Let the cookies cool on the baking sheet for 5 minutes, then transfer them to a wire rack to cool completely. Dust with powdered sugar before serving, if desired.

Storing & Reheating Easy 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: The cookie dough can be made ahead of time and refrigerated for up to 2 days.

Freezing Easy Pineapple Upside Down Sugar Cookies That Delight Every Bite

Freeze for up to 3 months. Thaw overnight in the refrigerator 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: Using a springform pan instead of a baking sheet can make it easier to remove the cookies from the pan after baking.
• Best substitution: For a gluten-free version, substitute the all-purpose flour with a 1:1 gluten-free flour blend.
• Make-ahead: The cookie dough can be made ahead of time and refrigerated for up to 2 days.
• Scaling: This recipe can be doubled or halved as needed.
• Troubleshooting: If the cookies are burning on the bottom, reduce the oven temperature to 350°F (175°C) and bake for an additional 2-3 minutes.

Easy Pineapple Upside Down Sugar Cookies That Delight Every Bite

⏱

Prep

15 minutes

🍳

Cook

12 minutes

⏳

Total

27 minutes

🍽

Serves

24 cookies

🥗

Diet

Gluten-free option available

Ingredients

Main Ingredients

• 1 can (20 oz) pineapple chunks
• 1/2 cup unsalted butter, melted
• 1/2 cup granulated sugar
• 1/2 cup brown sugar
• 1 large egg
• 1 tsp vanilla extract
• 1 1/2 cups all-purpose flour
• 1/2 tsp baking powder
• 1/4 tsp salt

Seasonings

• 1 tsp ground cinnamon
• 1/4 tsp ground nutmeg

Optional Toppings

• Chopped nuts (optional)
• Powdered sugar (optional)

Instructions

1. Prepare the pineapple: Drain the pineapple chunks, reserving 1/4 cup of juice. In a small bowl, mix the brown sugar and pineapple juice. Add the pineapple chunks and toss to coat. Let it marinate for 10 minutes.
2. Make the cookie dough: In a large bowl, mix the melted butter, granulated sugar, and brown sugar until well combined. Add the egg and vanilla extract, and mix until smooth. In a separate bowl, combine the flour, baking powder, salt, cinnamon, and nutmeg. Gradually add the dry ingredients to the wet ingredients, mixing just until combined.
3. Assemble the cookies: Preheat the oven to 375°F (190°C). Line a baking sheet with parchment paper or a silicone baking mat. Drop spoonfuls of cookie dough onto the baking sheet, leaving space between each cookie. Top each cookie with a spoonful of the marinated pineapple, including some of the brown sugar mixture. If desired, sprinkle with chopped nuts.
4. Bake the cookies: Bake for 10-12 minutes, or until the edges are golden brown. Let the cookies cool on the baking sheet for 5 minutes, then transfer them to a wire rack to cool completely. Dust with powdered sugar before serving, if desired.

Notes

• Chef tip: Using a springform pan instead of a baking sheet can make it easier to remove the cookies from the pan after baking.
• Best substitution: For a gluten-free version, substitute the all-purpose flour with a 1:1 gluten-free flour blend.
• Make-ahead: The cookie dough can be made ahead of time and refrigerated for up to 2 days.
• Scaling: This recipe can be doubled or halved as needed.
• Troubleshooting: If the cookies are burning on the bottom, reduce the oven temperature to 350°F (175°C) and bake for an additional 2-3 minutes.

Storage

• Fridge: Store in an airtight container at room temperature for up to 5 days.
• Freezer: Freeze for up to 3 months. Thaw overnight in the refrigerator 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: The cookie dough can be made ahead of time and refrigerated for up to 2 days.

Nutrition Per Serving

• Calories: 120
• Protein: 1g
• Fat: 5g
• Carbs: 18g
• Fiber: 1g
• Sugar: 12g
• Sodium: 60mg
• Cholesterol: 20mg
• Sat. Fat: 3g

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

Easy Pineapple Upside Down Sugar Cookies That Delight Every Bite FAQs

A Warm Final Note

I can’t wait for you to try Easy 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!