Pineapple Upside-Down Sugar Cookies

Pineapple Upside-Down Sugar Cookies are a delightful twist on the classic pineapple upside-down cake, but in a bite-sized, handheld form. With a soft sugar cookie base, caramelized pineapple, and a cherry on top, these cookies are a fun and visually stunning treat that combines tropical flavors with buttery sweetness.

Why You’ll Love This Recipe

1. Combines the classic dessert into an easy-to-eat cookie format.
2. A perfect balance of caramelized pineapple sweetness and buttery cookie dough.
3. Great for parties, potlucks, or as a unique dessert option.
4. Easy to make with simple ingredients.
5. A fun, tropical treat that’s sure to impress.

Ingredients

For the Caramelized Pineapple Topping

• Pineapple rings (fresh or canned)
• Maraschino cherries
• Unsalted butter
• Brown sugar

For the Sugar Cookie Dough

• All-purpose flour
• Baking powder
• Salt
• Unsalted butter, softened
• Granulated sugar
• Egg
• Vanilla extract

Directions

this recipe

Prepare the Pineapple Topping

1. Preheat the oven to 350°F (175°C). Grease a muffin tin generously.
2. In a small saucepan, melt butter and stir in brown sugar until dissolved. Spoon about 1 teaspoon of the mixture into each muffin cup.
3. Cut pineapple rings to fit the muffin cups (about 1 inch in diameter) and place one piece over the brown sugar mixture. Add a maraschino cherry in the center of each pineapple piece.

Make the Sugar Cookie Dough

4. In a medium bowl, whisk together flour, baking powder, and salt.
5. In a large bowl, cream softened butter and granulated sugar until light and fluffy. Add the egg and vanilla extract, mixing until combined.
6. Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.

Assemble and Bake

7. Scoop a heaping tablespoon of cookie dough and flatten it slightly. Place the dough over the pineapple and brown sugar layer in each muffin cup, pressing gently to cover the topping.
8. Bake for 12–15 minutes, or until the edges of the cookies are golden brown.
9. Let cool in the pan for 5 minutes before carefully inverting onto a serving plate.

Servings and Timing

• Servings: Makes 12 cookies
• Prep Time: 20 minutes
• Cook Time: 15 minutes
• Total Time: 35 minutes

Variations

• Coconut Twist: Add shredded coconut to the cookie dough for an extra tropical flavor.
• Spiced Flavor: Add a pinch of cinnamon or nutmeg to the brown sugar mixture for warmth.
• Mini Cookies: Use a mini muffin tin for bite-sized versions of these cookies.
• Nutty Topping: Sprinkle chopped pecans or walnuts over the brown sugar layer for added crunch.
• Gluten-Free: Use a gluten-free flour blend to accommodate dietary needs.

Storage/Reheating

• Storage: Store cookies in an airtight container at room temperature for up to 2 days or in the refrigerator for up to 4 days.
• Freezing: Freeze cookies in a single layer before transferring them to a freezer-safe bag. Freeze for up to 2 months and thaw overnight in the refrigerator.
• Reheating: Warm in the microwave for 10–15 seconds or enjoy at room temperature.

FAQs

1. Can I use fresh pineapple instead of canned?

Yes, fresh pineapple works beautifully for this recipe.

2. Do I need to grease the muffin tin?

Yes, greasing the tin is essential to prevent sticking and ensure the cookies release easily.

3. Can I use premade sugar cookie dough?

Yes, store-bought dough is a convenient option and works well.

4. How do I prevent the cookies from breaking when removing them from the pan?

Allow the cookies to cool slightly before inverting, and use a knife to gently loosen the edges if necessary.

5. Can I skip the cherries?

Absolutely! The cookies are still delicious without the cherries.

6. What if I don’t have a muffin tin?

You can use ramekins or a shallow cupcake tray as alternatives.

7. How do I make the topping extra caramelized?

Bake an additional 2–3 minutes, but watch closely to avoid burning the sugar.

8. Can I add rum for a tropical flair?

Yes, add a teaspoon of rum to the brown sugar mixture for an extra layer of flavor.

9. Are these cookies best served warm or cold?

They’re delicious both ways but are especially indulgent when served warm.

10. Can I make the dough ahead of time?

Yes, the cookie dough can be prepared and refrigerated for up to 24 hours before assembling.

Conclusion

Pineapple Upside-Down Sugar Cookies are a fun and delicious way to enjoy the flavors of a classic dessert in a portable format. Perfect for any occasion, these cookies are sure to impress with their beautiful presentation and tropical flavor. Try them today and bring a touch of the tropics to your table!

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