Pineapple Upside-Down Sugar Cookies

Ingredients (8–10 large cookies)

Topping:

4 tbsp butter

½ cup brown sugar

Pineapple rings (8–10 rings, well drained)

Maraschino cherries 

Sugar Cookie Dough:

½ cup butter, softened

1 cup granulated sugar

1 egg

2 tsp vanilla extract

1 ½ cups all-purpose flour

½ tsp baking soda

¼ tsp baking powder

¼ tsp salt

⭐ Instructions

1. Prep your pan

Line a large baking sheet with parchment paper.

Lightly grease the parchment so the caramel doesn’t

stick.

2. Make the caramel topping

1. Melt 4 tbsp butter in a small saucepan.

2. Stir in ½ cup brown sugar and cook until bubbly and

thick, about 1 minute.

3. Spoon a 1½–2 teaspoon puddle of caramel on the

parchment for each cookie.

4. Place one pineapple ring on top of each caramel

puddle.

5. Add one cherry in the center of the ring.

3. Make the sugar cookie dough

1. Cream together butter + granulated sugar until fluffy.

2. Beat in egg + vanilla.

3. Mix in flour, baking soda, baking powder, salt until a

soft dough forms.

4. Assemble cookies

Scoop 2–3 tablespoons of cookie dough per cookie.

Flatten slightly with your hands.

Place each flattened dough disc directly on top of its

pineapple ring, pressing lightly so it sticks.

5. Bake

Bake at 350°F (175°C) for 12–15 minutes, until the

cookie edges are lightly golden.

Let them cool 8–10 minutes — this helps the caramel

set.

Carefully flip each cookie over so the pineapple ring is on

top.