Pineapple Upside-Down Sugar Cookies
⏱ Time
Prep: 20 minutes
Bake: 12–14 minutes
Total: ~35 minutes
🍽 Yield
About 18–20 cookies
🛒 Ingredients
Pineapple Topping
¼ cup unsalted butter, melted
½ cup brown sugar (light or dark)
6–7 pineapple rings, well-drained and cut into small pieces
Maraschino cherries, halved (optional)
Sugar Cookie Dough
½ cup unsalted butter, softened
¾ cup granulated sugar
1 large egg
1 tsp vanilla extract
1 ½ cups all-purpose flour
½ tsp baking powder
¼ tsp baking soda
¼ tsp salt
🔪 Instructions
1. Prep the Pan
Preheat oven to 350°F (175°C).
Line a muffin tin with paper liners or lightly grease each cup.
2. Make the Pineapple Base
Spoon 1 teaspoon melted butter into each muffin cup.
Sprinkle 1 tablespoon brown sugar over the butter.
Add a few pineapple pieces on top.
Place a cherry half in the center (optional).
3. Make the Sugar Cookie Dough
In a bowl, cream softened butter and sugar until light and fluffy.
Beat in egg and vanilla.
In a separate bowl, whisk flour, baking powder, baking soda, and salt.
Gradually mix dry ingredients into wet ingredients until combined.
4. Assemble
Scoop about 1½ tablespoons of cookie dough.
Flatten slightly and place over the pineapple topping in each muffin cup.
Gently press so the dough covers the fruit.
5. Bake
Bake for 12–14 minutes, until lightly golden and set.
6. Flip & Cool
Let cookies cool in the pan for 5 minutes.
Carefully invert onto a baking sheet or plate.
Cool slightly before serving.
⭐ Tips
Drain pineapple very well to avoid soggy cookies.
Don’t overbake — soft centers are best.
Store in an airtight container for up to 3 days.
🍒 Optional Variations
Coconut twist: Add ¼ tsp coconut extract to dough.
Spiced: Add a pinch of cinnamon to the brown sugar layer.
Mini version: Use a mini muffin tin (bake 8–10 minutes).