Pineapple Upside-Down Sugar Cookies

Instructions

Step 1: Prepare the Pineapple Topping

1. Prep the Pineapple: Drain the canned pineapple rings and pat dry with paper towels. Cut each ring into small chunks, roughly the size of a quarter.
2. Assemble Topping: Place a teaspoon of brown sugar in the center of each cookie mold or lined muffin tin, then place a small pineapple piece and half of a cherry on top of the brown sugar. Set aside.

Step 2: Make the Cookie Dough

1. Cream Butter and Sugar: In a large mixing bowl, beat the softened butter, granulated sugar, and brown sugar together until light and fluffy, about 2-3 minutes.
2. Add Wet Ingredients: Add the egg and vanilla extract to the butter mixture, beating until well combined.
3. Combine Dry Ingredients: In a separate bowl, whisk together flour, baking powder, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Be careful not to overmix.

Step 3: Assemble and Bake

1. Add Dough on Top of Topping: Scoop a tablespoon of cookie dough and press it gently over the pineapple and cherry in each muffin cup, flattening slightly to cover.
2. Bake: Bake in a preheated 350°F (175°C) oven for 12-15 minutes, or until the edges are lightly golden and the cookies feel set.
3. Cool and Invert: Allow cookies to cool for 5 minutes in the pan. Run a knife around the edges and gently invert each cookie onto a wire rack. If any fruit pieces stick, gently press them back onto the cookie.

Step 4: Serve and Enjoy!

1. Serve Warm or at Room Temperature: These cookies are delightful when served warm as the caramelized pineapple topping is at its most flavorful.
2. Store: Keep leftovers in an airtight container at room temperature for up to 3 days.

Tips for Perfect Pineapple Upside-Down Sugar Cookies

• Use Fresh Pineapple for a Twist: Fresh pineapple can also be used instead of canned for an extra burst of flavor.
• Reserve Pineapple Juice for Extra Moisture: If your dough feels a bit dry, add a teaspoon of reserved pineapple juice for added moisture and flavor.
• Decorate with More Fruit: Add a little extra cherry on top after baking for a festive finish.

Conclusion

Pineapple Upside-Down Sugar Cookies are a delightful treat that packs all the tropical flavor of pineapple upside-down cake into a handheld dessert. The caramelized fruit paired with a soft sugar cookie base is a winning combination that will have everyone asking for more. Enjoy this easy and tropical twist on classic flavors, and bring a little sunshine to your dessert table!