Ingredients
For the Cookie Base:
- Unsalted Butter (½ cup, softened) – Gives the cookies their rich, buttery texture. If using salted butter, reduce the added salt.
- Granulated Sugar (¾ cup) – Provides sweetness and helps with the cookie’s soft structure. Brown sugar can be used for a deeper caramel-like flavor.
- Large Egg (1) – Binds the ingredients together and adds moisture. If allergic to eggs, substitute with a flax egg (1 tbsp ground flaxseed + 3 tbsp water).
- Vanilla Extract (1 tsp) – Enhances the sweetness with warm, aromatic notes.
- All-Purpose Flour (1 ¼ cups) – Forms the cookie’s structure. If needed, use a 1:1 gluten-free flour blend.
- Baking Powder (½ tsp) – Helps the cookies rise slightly and stay soft.
- Salt (¼ tsp) – Balances sweetness and enhances flavors.
For the Topping:
- Brown Sugar (½ cup) – Caramelizes during baking, creating the signature upside-down effect.
- Melted Butter (2 tbsp) – Helps the brown sugar create a rich, syrupy base.
- Pineapple Rings (1 small can, cut into smaller pieces) – Provides the tropical fruitiness. Fresh pineapple works too but should be cut into small tidbits for even baking.
- Maraschino Cherries (halved) – Adds a pop of color and sweetness. Fresh cherries or dried cranberries can be used as alternatives.
Instructions
1. Prepare the Cookie Dough
- Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone baking mat.
- In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy. This can be done with an electric mixer or by hand using a whisk. Proper creaming ensures a soft and tender cookie.
- Add the egg and vanilla extract, mixing until well combined. The batter should become smooth and slightly glossy.
- In a separate bowl, whisk together the all-purpose flour, baking powder, and salt.
- Gradually add the dry ingredients to the wet mixture, stirring just until a soft dough forms. Avoid overmixing, as this can lead to tough cookies.
2. Prepare the Topping
- In a small bowl, mix the melted butter and brown sugar until smooth. This will create the caramelized topping for each cookie.
- Spoon about 1 teaspoon of the brown sugar mixture onto the lined baking sheet, spacing them apart to allow room for cookie spreading.
3. Assemble the Cookies
- Place a small piece of pineapple (or pineapple tidbits) on top of each brown sugar base.
- Add a maraschino cherry half in the center of the pineapple for a classic touch.
- Scoop about 1 ½ tablespoons of cookie dough, flatten it slightly with your hands, and place it over the pineapple and brown sugar mixture. Gently press the dough to cover the fruit, ensuring the edges seal the topping.
4. Bake the Cookies
- Bake in the preheated oven for 12-15 minutes, or until the cookies turn golden around the edges.
- Remove from the oven and let them cool on the baking sheet for 5 minutes before carefully transferring them to a wire rack. Allowing them to cool helps set the caramelized topping.
5. Serve and Enjoy
- Once completely cooled, flip the cookies upside-down to reveal the beautiful pineapple-cherry topping. Enjoy as a snack, dessert, or party treat!
Notes
- Dough too sticky? Chill it in the fridge for 10-15 minutes before handling. This makes it easier to shape.
- Cookies spreading too much? Ensure your butter isn’t overly softened. Slightly cold butter helps cookies hold their shape.
- Pineapple releasing too much juice? Pat the pineapple pieces dry with a paper towel before using. Too much moisture can cause soggy cookies.
- Cookies sticking to the pan? Use parchment paper or a silicone baking mat to prevent sticking and make cleanup easier.
- Want crispier edges? Bake for an extra 2 minutes, but watch carefully to prevent burning.
- Prep Time: 15 minutes
- Cook Time: 12-15 minutes