Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies are a delightful take on a classic dessert. With the soft, buttery texture of sugar cookies and the sweet-tart flavors of caramelized pineapple and cherries, they bring the best of both worlds to your dessert table. The cookies start with a rich base of creamed butter and sugar, enhanced by a hint of vanilla and an egg for a perfectly moist dough. Flour, baking soda, and salt add structure and balance, while the topping is a simple but delicious blend of melted butter and brown sugar, creating a caramel-like glaze for the fruit.

INGREDIENTS

• Unsalted butter (melted): 1/4 cup for the caramelized topping
• Brown sugar: 1/3 cup for topping
• Pineapple slices: 12, from canned
• Maraschino cherries: 12
• Granulated sugar: 1 cup
• Unsalted butter (softened): 1/2 cup for cookie dough
• Large egg: 1
• Vanilla extract: 1 tsp
• All-purpose flour: 1 1/2 cups
• Salt: 1/4 tsp
• Baking soda: 1/4 tsp

INSTRUCTIONS

Step 1:

Preheat oven to 350°F. Mix melted butter and brown sugar together. Place a teaspoon of the mixture into each muffin tin compartment, then add a pineapple slice and a maraschino cherry on top.

Step 2:

In a large bowl, cream together granulated sugar and softened butter until light and fluffy. Beat in the egg and vanilla extract.

Step 3:

In a separate bowl, whisk together flour, salt, and baking soda. Gradually add the dry ingredients to the wet mixture until fully combined.

Step 4:

Form dough balls and flatten slightly. Place each on top of the pineapple and cherry in the muffin tin compartments.

Step 5:

Bake for 14-16 minutes, or until the cookies are golden brown.

Step 6:

Let cookies cool in the muffin tin for 5 minutes, then gently remove.

Serving and Storage Tips

• Serve warm for the best caramelized flavor.
• Store in an airtight container for up to 3 days at room temperature or refrigerate for a week.

Helpful Notes

• For a more intense flavor, use fresh pineapple instead of canned.
• Ensure the butter and sugar mixture is evenly distributed to prevent sticking.

Tips from Well-Known Chefs

• Chef Clara recommends using silicone muffin tins for easier removal of the cookies.
• Add a dash of cinnamon to the topping for a warm spice note.

Classic Dessert with a Twist

These cookies put a fun spin on traditional pineapple upside-down cake, offering a bite-sized treat that’s easy to make and serve.

Rich, Sweet, and Perfectly Balanced

The caramelized brown sugar, tart pineapple, and buttery sugar cookie combine for an irresistible flavor profile that will have guests asking for more.

FAQs

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple can be used, but make sure to cut it into thin slices.

Do I need to grease the muffin tin?

It’s recommended to lightly grease the muffin tin to prevent sticking.

Can I substitute the maraschino cherries?

Yes, you can use fresh cherries or even omit them if preferred.

How do I store leftovers?

Store in an airtight container at room temperature for up to 3 days or refrigerate for up to a week.

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Conclusion

Pineapple Upside Down Sugar Cookies combine the soft, buttery texture of sugar cookies with a sweet and tangy topping of caramelized pineapple slices and cherries. The cookies are baked upside down in muffin tins, ensuring that every bite is filled with fruity goodness and rich, caramelized brown sugar. Easy to make and visually impressive, these cookies are perfect for parties, family gatherings, or whenever you want to surprise your guests with a unique treat. With just the right amount of sweetness and a beautiful presentation, these cookies bring a taste of summer to any table.