Pineapple Upside Down Sugar Cookies That Delight Every Bite

Pineapple Upside Down Sugar Cookies are the ultimate tropical treat that’s crispy on the outside and soft on the inside. After making these many times, I’ve discovered the trick to getting that perfect golden crust. Keep reading for my best tips, or jump straight to the recipe card. If you love recipes like this, you’ll also enjoy Easy Pineapple Chicken and Rice One-Pan Wonder and Strawberry Shortcake Muffins Recipe Easy 5-Minute Quick Snack Idea.

What You'll Need for 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.

• 1/2 cup unsalted butter, softened
• 1/2 cup granulated sugar
• 1 large egg
• 1 teaspoon vanilla extract
• 1 1/2 cups all-purpose flour
• 1/2 teaspoon baking powder
• 1/4 teaspoon salt
• 1 can (20 oz) pineapple slices, drained
• 1/2 teaspoon ground cinnamon
• 1/4 teaspoon ground nutmeg
• Optional: Maraschino cherries, for garnish

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

1. Step 1: Preheat oven to 375°F (190°C). Grease a 12-cup muffin tin.
2. Step 2: In a large bowl, cream together butter and sugar until light and fluffy. Beat in egg and vanilla extract.
3. Step 3: In another bowl, combine flour, baking powder, cinnamon, and nutmeg. Gradually add dry ingredients to wet ingredients, mixing just until combined.
4. Step 4: Press pineapple slices into the bottom of each muffin cup. Spoon cookie dough over pineapple, pressing down gently to flatten.
5. Step 5: Bake for 18-20 minutes or until golden brown. Let cool in pan for 5 minutes, then invert onto a wire rack to cool completely. Garnish with maraschino cherries if desired.

Storing & Reheating 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 in the refrigerator for up to 1 week. Make-ahead tip: Prepare dough ahead of time and refrigerate for up to 2 days. Bake as directed.

Freezing Pineapple Upside Down Sugar Cookies That Delight Every Bite

Freeze cooled cookies in an airtight container for up to 3 months. Thaw at room temperature before serving.

How to Reheat Without Drying It Out

Oven: Reheat in a preheated 350°F (175°C) oven for 5-7 minutes or until warmed through. Microwave: Reheat in the microwave for 10-15 seconds or until warmed through. (Microwaving may soften the crust.)

Recipe Notes

• Chef tip: For a gluten-free version, substitute all-purpose flour with a 1:1 gluten-free flour blend.
• Make-ahead: Prepare dough ahead of time and refrigerate for up to 2 days. Bake as directed.
• Scaling: This recipe can be doubled to make 24 cookies.
• Troubleshooting: If cookies are browning too quickly, tent the pan with aluminum foil for the remaining baking time.

Pineapple Upside Down Sugar Cookies That Delight Every Bite

⏱

Prep

15 mins

🍳

Cook

20 mins

⏳

Total

35 mins

🍽

Serves

12 cookies

🥗

Diet

Gluten-Free (optional)

Ingredients

Main Ingredients

• 1/2 cup unsalted butter, softened
• 1/2 cup granulated sugar
• 1 large egg
• 1 teaspoon vanilla extract
• 1 1/2 cups all-purpose flour
• 1/2 teaspoon baking powder
• 1/4 teaspoon salt
• 1 can (20 oz) pineapple slices, drained

Seasonings

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

Optional Toppings

• Maraschino cherries, for garnish

Instructions

1. Step 1: Preheat oven to 375°F (190°C). Grease a 12-cup muffin tin.
2. Step 2: In a large bowl, cream together butter and sugar until light and fluffy. Beat in egg and vanilla extract.
3. Step 3: In another bowl, combine flour, baking powder, cinnamon, and nutmeg. Gradually add dry ingredients to wet ingredients, mixing just until combined.
4. Step 4: Press pineapple slices into the bottom of each muffin cup. Spoon cookie dough over pineapple, pressing down gently to flatten.
5. Step 5: Bake for 18-20 minutes or until golden brown. Let cool in pan for 5 minutes, then invert onto a wire rack to cool completely. Garnish with maraschino cherries if desired.

Notes

• Chef tip: For a gluten-free version, substitute all-purpose flour with a 1:1 gluten-free flour blend.
• Make-ahead: Prepare dough ahead of time and refrigerate for up to 2 days. Bake as directed.
• Scaling: This recipe can be doubled to make 24 cookies.
• Troubleshooting: If cookies are browning too quickly, tent the pan with aluminum foil for the remaining baking time.

Storage

• Fridge: Store in an airtight container in the refrigerator for up to 1 week.
• Freezer: Freeze cooled cookies in an airtight container for up to 3 months. Thaw at room temperature before serving.
• Oven reheat: Reheat in a preheated 350°F (175°C) oven for 5-7 minutes or until warmed through.
• Microwave reheat: Reheat in the microwave for 10-15 seconds or until warmed through. (Microwaving may soften the crust.)
• Make ahead: Prepare dough ahead of time and refrigerate for up to 2 days. Bake as directed.

Nutrition Per Serving

• Calories: 120
• Protein: 1g
• Fat: 5g
• Carbs: 17g
• Fiber: 0g
• Sugar: 10g
• Sodium: 50mg
• Cholesterol: 25mg
• Sat. Fat: 3g

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

Pineapple Upside Down Sugar Cookies That Delight Every Bite FAQs

A Warm Final Note

I can’t wait for you to try 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!