Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite
Crispy Pineapple Upside Down Sugar Cookies are the perfect blend of tender cookie and caramelized pineapple. After making these many times, I’ve discovered the trick to a golden, crispy exterior and a soft, moist interior. Jump to the recipe card or keep reading for my best tips. If you love recipes like this, you’ll also enjoy Golden Crust Garlic Rosemary Focaccia Muffins and Creamy Swirl Ice Cream Bread Treat.
Why This Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite Is Pure Comfort
- Crispy edges with a soft center
- Caramelized pineapple topping
- Easy and quick to make
- Perfect for any occasion
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
- 1 teaspoon vanilla extract
- 2 1/2 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 (20 oz) can pineapple slices in juice, drained
- 1/2 teaspoon ground cinnamon
- 1/4 teaspoon ground nutmeg
- Optional: Whipped cream, for serving
📝 Ingredient Notes
- Pineapple slices: Reserve 1/4 cup of pineapple juice for the cookie dough.
🛒 Tools & Equipment I Recommend
- Silicone baking mat — Prevents cookies from sticking and ensures even baking. → See on Amazon
- Pineapple slicer — Makes quick work of slicing pineapple for this recipe. → See on Amazon
How to Make Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite
- Prepare the cookie dough: Cream together butter and sugar until light and fluffy. Beat in egg and vanilla extract. In a separate bowl, combine flour, baking soda, salt, cinnamon, and nutmeg. Gradually add dry ingredients to wet ingredients, mixing just until combined. Stir in reserved pineapple juice.
- Prepare the pan: Preheat oven to 375°F (190°C). Grease a 9×13-inch baking pan or line with parchment paper. Arrange pineapple slices in a single layer in the pan.
- Assemble the cookies: Press cookie dough evenly over pineapple slices, using your fingers or the bottom of a measuring cup to press down and create an even layer.
- Bake: Bake for 25-30 minutes, or until edges are golden brown and a toothpick inserted into the center comes out clean. Allow to cool in the pan for 10 minutes, then invert onto a serving platter.
- Serve: Serve warm or at room temperature, with whipped cream if desired.
Cook's Tips for Perfect Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite
- Pro tip: Press the cookie dough evenly to ensure even baking and crispy edges.
- Common mistake and fix: If your cookies turn out dry, you may have overbaked them. To prevent this, keep a close eye on the baking time and use the toothpick test to check for doneness.
- Pro tip: For a prettier presentation, use a cookie cutter to cut out the cookies after inverting the pan.
- Pro tip: Store leftover cookies in an airtight container at room temperature for up to 5 days.
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: The cookie dough can be made ahead of time and refrigerated for up to 2 days.
Freezing Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite
Not recommended for freezing.
How to Reheat Without Drying It Out
Oven: Not necessary, as these are best enjoyed fresh. Microwave: Not recommended, as this may make the cookies soggy.
Recipe Notes
- Chef tip: For a more caramelized topping, sprinkle the pineapple slices with a little brown sugar before adding the cookie dough.
- Best substitution: You can substitute the pineapple slices with apple slices for a different flavor.
- Make-ahead: The cookie dough can be made ahead of time and refrigerated for up to 2 days.
- Scaling: This recipe can be halved or doubled to suit your needs.
- Troubleshooting: If your cookies are not crispy, you may need to bake them for a few more minutes. However, be careful not to overbake them, as this can cause them to become dry.
Want to level up this recipe?
Pineapple corer — Makes quick work of coring pineapple for this recipe. → Check price on Amazon
Crispy Pineapple Upside Down Sugar Cookies That Delight Every Bite
Ingredients
Main Ingredients
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 1/2 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 (20 oz) can pineapple slices in juice, drained
Seasonings
- 1/2 teaspoon ground cinnamon
- 1/4 teaspoon ground nutmeg
Optional Toppings
- Whipped cream, for serving
Instructions
- Prepare the cookie dough: Cream together butter and sugar until light and fluffy. Beat in egg and vanilla extract. In a separate bowl, combine flour, baking soda, salt, cinnamon, and nutmeg. Gradually add dry ingredients to wet ingredients, mixing just until combined. Stir in reserved pineapple juice.
- Prepare the pan: Preheat oven to 375°F (190°C). Grease a 9×13-inch baking pan or line with parchment paper. Arrange pineapple slices in a single layer in the pan.
- Assemble the cookies: Press cookie dough evenly over pineapple slices, using your fingers or the bottom of a measuring cup to press down and create an even layer.
- Bake: Bake for 25-30 minutes, or until edges are golden brown and a toothpick inserted into the center comes out clean. Allow to cool in the pan for 10 minutes, then invert onto a serving platter.
- Serve: Serve warm or at room temperature, with whipped cream if desired.
Notes
- Chef tip: For a more caramelized topping, sprinkle the pineapple slices with a little brown sugar before adding the cookie dough.
- Best substitution: You can substitute the pineapple slices with apple slices for a different flavor.
- Make-ahead: The cookie dough can be made ahead of time and refrigerated for up to 2 days.
- Scaling: This recipe can be halved or doubled to suit your needs.
- Troubleshooting: If your cookies are not crispy, you may need to bake them for a few more minutes. However, be careful not to overbake them, as this can cause them to become dry.
Storage
- Fridge: Store in an airtight container at room temperature for up to 5 days.
- Freezer: Not recommended for freezing.
- Oven reheat: Not necessary, as these are best enjoyed fresh.
- Microwave reheat: Not recommended, as this may make the cookies soggy.
- Make ahead: The cookie dough can be made ahead of time and refrigerated for up to 2 days.
Nutrition Per Serving
- Calories: 180
- Protein: 2g
- Fat: 8g
- Carbs: 25g
- Fiber: 1g
- Sugar: 12g
- Sodium: 120mg
- Cholesterol: 30mg
- Sat. Fat: 5g
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
Yes, the cookie dough can be made ahead of time and refrigerated for up to 2 days. However, these cookies are best enjoyed fresh.
You may have overbaked them. To prevent this, keep a close eye on the baking time and use the toothpick test to check for doneness.
Not recommended, as freezing can cause the cookies to become dry and crumbly.
No, this recipe is not suitable for the air fryer.
Store in an airtight container at room temperature for up to 5 days.
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!
