Pineapple Upside Down Sugar Cookies That Delight Every Bite

Pineapple Upside Down Sugar Cookies

These cookies are a delightful fusion of a classic tropical cake and a soft, chewy sugar cookie. Each bite features a caramelized pineapple ring, a sweet maraschino cherry center, and a buttery cookie base that soaks up all the fruity juices.

🛒 Ingredients

The Fruity Topping

Pineapple Slices: 1 can (20 oz) sliced pineapple in juice (well-drained and patted dry).

Maraschino Cherries: 12–15 cherries (stems removed).

Unsalted Butter: 4 tablespoons, melted.

Light Brown Sugar: ½ cup, packed.

The Sugar Cookie Base

Unsalted Butter: 1 cup (2 sticks), softened to room temperature.

Granulated Sugar: 1 cup.

Large Egg: 1, room temperature.

Vanilla Extract: 1 ½ teaspoons.

All-Purpose Flour: 2 ¾ cups.

Baking Powder: 1 teaspoon.

Salt: ½ teaspoon.

👩‍🍳 Instructions

1. Prepare the Pan and Topping

Preheat your oven to $350^{\circ}\text{F}$ ($175^{\circ}\text{C}$).

Prep the Slices: Take your pineapple slices and pat them very dry with paper towels. If they are too wet, the cookies will become soggy.

The Glaze: In a small bowl, whisk together the melted butter and brown sugar until it forms a thick paste.

Layout: Line a large baking sheet with parchment paper or a silicone baking mat. Place about 1 tablespoon of the brown sugar mixture in small mounds spaced 3 inches apart. Place a pineapple slice directly on top of each mound, and tuck a cherry into the center hole of each pineapple.

2. Make the Cookie Dough

Creaming: In a large bowl or stand mixer, cream together the softened butter and granulated sugar until light and fluffy (about 2–3 minutes).

Wet Ingredients: Add the egg and vanilla extract. Beat until well combined.

Dry Ingredients: In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet ingredients, mixing on low speed just until a dough forms. Do not overmix.

3. Assemble and Bake

Scooping: Take about 3 tablespoons of dough (a large cookie scoop) and flatten it slightly into a disc.

Covering: Place the dough disc directly over the pineapple slice. Gently press the edges down so the dough "hugs" the pineapple. The dough should completely cover the top of the fruit.

Bake: Bake for 14–16 minutes, or until the edges of the cookies are just starting to turn a very light golden brown.

The Flip: This is the crucial part! Let the cookies sit on the pan for exactly 5 minutes. While still warm, carefully flip them over using a wide spatula so the pineapple side is now facing up.

💡 Pro-Tips for Success

Moisture Control: Ensure the pineapple slices are bone-dry before placing them on the sugar mixture. Moisture is the enemy of a crisp cookie.

The Timing of the Flip: If you wait too long to flip, the brown sugar caramel will harden and stick to the parchment paper. If you flip too soon, the cookie might break. 5 minutes is the "sweet spot."

Size Matters: If your pineapple slices are standard size, you may only fit 6–8 cookies per sheet. Bake in batches to avoid crowding.

Storage: These are best served the day they are made. If you have leftovers, store them in a single layer in an airtight container in the refrigerator for up to 2 days.