Pineapple Upside-Down Sugar Cookies
Intro:
Pineapple Upside-Down Sugar Cookies are a delightful mash-up of two favorites: buttery sugar cookies and the iconic pineapple upside-down cake. These cookies are soft and chewy with a slightly crisp edge, topped with a gooey brown sugar-pineapple layer that caramelizes beautifully as they bake. A maraschino cherry in the center adds a nostalgic, colorful pop. Perfect for parties, holidays, or when you’re craving a fruity dessert that feels both classic and fresh!
Prep Time: 15 minutes
Chill Time (optional): 30 minutes
Bake Time: 12–15 minutes
Total Time: ~45 minutes (with chill) or ~25 minutes (no chill)
Ingredients:
For the Topping:
½ cup light brown sugar
2 tbsp melted butter
10–12 pineapple rings, cut into small chunks or pieces
10–12 maraschino cherries, halved
For the Sugar Cookie Dough:
1 cup unsalted butter, softened
1 cup granulated sugar
1 egg
1 ½ tsp vanilla extract
2 ½ cups all-purpose flour
½ tsp baking soda
¼ tsp salt
Instructions:
Prep the Topping
In a small bowl, mix brown sugar and melted butter until combined.
Lightly grease or line a muffin tin (standard size works great for shaping).
Spoon 1 tsp of the brown sugar-butter mixture into each muffin cup.
Place a small pineapple chunk and half a cherry (cut side up) on top of the sugar mixture in each cup.
Make the Cookie Dough
In a large bowl, cream together butter and sugar until light and fluffy (2–3 minutes).
Beat in the egg and vanilla extract.
In another bowl, whisk together flour, baking soda, and salt.
Gradually add the dry ingredients to the wet mixture, mixing just until combined.
Chill dough for 30 minutes (optional but helps prevent spreading).
Assemble
Roll about 1 ½ tbsp of dough into a ball and flatten slightly.
Place the dough disc over the pineapple/cherry topping in the muffin tin and press gently to spread.
Bake
Preheat oven to 350°F (175°C).
Bake for 12–15 minutes, or until the edges are lightly golden.
Cool in the tin for 5 minutes, then carefully invert the pan onto a tray or parchment paper while cookies are still warm.
Don’t let them cool completely in the tin or the caramel may harden and stick!
Tips & Variations:
No Muffin Tin? Use parchment-lined baking sheets and shape small pineapple pieces/cherry under each cookie manually.
Add a bit of pineapple juice to the sugar mixture for extra flavor.
Use crushed pineapple, drained well, if you prefer finer topping bits.
Add a dash of cinnamon or coconut flakes to the dough for a twist.
Serving Suggestions:
Serve slightly warm for gooey caramel topping.
Pair with vanilla ice cream for a dessert plate.
Dust with powdered sugar for extra flair.
Nutrition (Per Cookie – Approx.):
Calories: 160
Fat: 8g
Carbohydrates: 22g
Sugar: 14g
Protein: 1g
Sodium: 70mg