Introduction

Upside-Down Cookies are a delightful twist on traditional cookies, featuring a caramelized pineapple and cherry topping that makes each bite sweet and fruity. These soft, buttery treats bring a tropical flair perfect for any occasion.

A white plate holds a stack of round pineapple cookies with a bright yellow pineapple ring shape on top of each. At the center of every cookie sits a glossy, deep red cherry filling. The cookies have a crumbly golden-brown base visible around the edges, and the pineapple rings have a shiny, slightly translucent texture that contrasts with the smooth, rich red center. The cookies are stacked in two layers with some spread around the plate, all resting on a white marbled surface. photo taken with an iphone --ar 4:5 --v 7

Ingredients

½ cup unsalted butter, softened
¾ cup granulated sugar
1 large egg
1 tsp vanilla extract
1 ¼ cups all-purpose flour
½ tsp baking powder
¼ tsp salt
½ cup brown sugar
2 tbsp melted butter
1 small can pineapple rings, cut into smaller pieces
Maraschino cherries, halved

Instructions

Step 1: Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone baking mat.
Step 2: In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy, using an electric mixer or whisk.
Step 3: Add the egg and vanilla extract, mixing until the batter is smooth and slightly glossy.
Step 4: In a separate bowl, whisk together the flour, baking powder, and salt.
Step 5: Gradually add the dry ingredients to the wet mixture, stirring just until a soft dough forms. Avoid overmixing.
Step 6: In a small bowl, combine the melted butter and brown sugar until smooth.
Step 7: Spoon about 1 teaspoon of the brown sugar mixture onto the lined baking sheet, spacing them apart to allow for spreading.
Step 8: Place a small piece of pineapple on each brown sugar base, then add a halved maraschino cherry in the center of the pineapple.
Step 9: Scoop about 1 ½ tablespoons of cookie dough, flatten it slightly, and place it over the pineapple and brown sugar. Gently press the edges to seal the topping.
Step 10: Bake for 12-15 minutes, until the cookies are golden at the edges.
Step 11: Let the cookies cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
Step 12: Once cool, flip each cookie upside-down to reveal the caramelized pineapple and cherry topping before serving.

Tips & Variations

Use brown sugar instead of granulated sugar for a richer caramel flavor in the dough.
Substitute fresh pineapple tidbits if canned is not available, ensuring they are cut into small pieces.
For a gluten-free option, replace all-purpose flour with a 1:1 gluten-free flour blend.
If allergic to eggs, use a flax egg by mixing 1 tablespoon ground flaxseed with 3 tablespoons water; let it sit before adding.
Try dried cranberries or fresh cherries instead of maraschino cherries for a different taste and texture.

Storage

Store upside-down cookies in an airtight container at room temperature for up to 4 days. To keep them fresh longer, refrigerate for up to one week. Reheat briefly in a warm oven or microwave to soften the caramelized topping before serving.

How to Serve

A plate with a stack of six round pineapple upside-down mini cakes is shown on a white marbled surface. Each cake has two layers: the top layer is a shiny, golden yellow pineapple ring with a juicy texture, and the center is filled with a bright red glazed cherry. The bottom layer is a moist, golden brown cake base that looks soft and slightly crumbly. The cakes are stacked in a slightly uneven pile, showing the layers clearly from the side. photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I use salted butter instead of unsalted?

Yes, but reduce or omit any additional salt in the recipe to prevent the cookies from becoming too salty.

How do I prevent the topping from sticking to the baking sheet?

Line the baking sheet with parchment paper or a silicone mat to ensure the caramelized topping releases easily when flipping the cookies.