These sweet, cheerful cookies are a playful take on the traditional pineapple upside-down cake — but in fun, portable cookie form! Soft, chewy, and topped with caramelized pineapple and cherries, they’re perfect for parties, gifting, or a tropical treat at home.
Why You’ll Love These Cookies
If you love the buttery sweetness of pineapple upside-down cake but want something quicker and more snackable, these cookies are the answer. With a caramelized brown sugar base, fruity topping, and tender vanilla cookie, each bite is like sunshine on a spoon. No cake pans, no fuss — just pure, delicious fun!
They’re easy enough for a weeknight baking session and pretty enough to impress at a gathering. Plus, they store well and make adorable gifts tied with a ribbon.
Ingredients You’ll Need
- Unsalted Butter (½ cup, softened): Creamy and rich, it’s the base of a tender cookie texture
- Granulated Sugar (¾ cup): Adds sweetness and helps the dough cream perfectly
- Large Egg (1): Helps bind the dough while adding richness
- Vanilla Extract (1 tsp): Adds warmth and enhances the pineapple flavor
- All-Purpose Flour (1¼ cups): Gives structure while keeping the cookies soft
- Baking Powder (½ tsp): Helps them rise gently without spreading too much
- Salt (¼ tsp): Balances all the sweetness
- Brown Sugar (½ cup): Creates a delicious caramelized base for the fruit
- Melted Butter (2 tbsp): Mixes with the brown sugar for that signature sticky top
- Pineapple Rings (1 small can, chopped): Brings juicy, tropical flavor to each bite
- Maraschino Cherries (halved): Classic and colorful, they complete the upside-down look
How to Make Pineapple Upside-Down Cookies
Step 1: Prep the Oven and Pan
Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper or a silicone mat.
Step 2: Cream Butter and Sugar
In a mixing bowl, cream the softened butter with the granulated sugar until the mixture is fluffy and pale. Use a hand mixer or whisk.
Step 3: Add Egg and Vanilla
Beat in the egg and vanilla extract until the batter becomes smooth and glossy.
Step 4: Mix Dry Ingredients
In a separate bowl, whisk together the flour, baking powder, and salt.
Step 5: Combine Wet and Dry
Gradually stir the dry mixture into the wet ingredients until a soft dough forms. Be careful not to overmix.
Step 6: Make the Caramel Base
In a small bowl, combine the brown sugar and melted butter. This will be the gooey base for your fruit topping.
Step 7: Assemble Fruit Topping
Spoon about 1 teaspoon of the brown sugar mixture onto your baking sheet, spaced a few inches apart.
Top each spoonful with a piece of chopped pineapple and half a cherry.
Step 8: Cover with Cookie Dough
Scoop out 1½ tablespoons of dough, flatten slightly, and place over the fruit-topped sugar mix. Gently press and seal the edges.
Step 9: Bake
Bake for 12–15 minutes or until the edges are golden and the tops look set.
Step 10: Cool and Flip
Let the cookies cool on the tray for 5 minutes, then transfer to a wire rack. Once fully cooled, flip the cookies upside-down to reveal their glossy, golden pineapple tops.
Why It Works
This recipe combines the nostalgic flavor of pineapple upside-down cake with the simplicity of cookie baking. The brown sugar base caramelizes in the oven, infusing the fruit with a rich, buttery glaze. The soft vanilla cookie holds everything together without overpowering the tropical topping. It’s indulgent, playful, and crowd-pleasing — all in one!
Tips & Tools
- Cookie Scoop: Helps portion evenly for consistent results.
- Chop Pineapple Small: Keeps the topping from overpowering the cookie.
- Don’t Skip Parchment Paper: Makes flipping easy and prevents sticking.
- Cooling Is Key: Flipping too early can cause breakage, so be patient.
- Mix Up the Fruit: Try mango, peach, or even blueberries for a twist.
Final Thoughts
These Pineapple Upside-Down Cookies are more than just adorable — they’re completely irresistible. Whether you’re baking for a party or just want a tropical escape in dessert form, they deliver buttery flavor, fruity sweetness, and that classic upside-down magic in every bite.
Serve with tea, share with friends, or keep them all to yourself (we won’t tell 😉)