If you love pineapple upside-down cake, you’re going to adore these Pineapple Upside Down Sugar Cookies. They take everything you love about the classic dessert — caramelized pineapple, buttery sweetness, nostalgic flavor — and turn it into a soft, melt-in-your-mouth cookie.
Each cookie starts with a rich sugar cookie base and gets topped with a pineapple ring and a sprinkle of sugar that caramelizes beautifully in the oven. The result? A tropical twist on a timeless favorite that’s perfect for potlucks, parties, or whenever you need a bright, cheerful dessert.
Why You’ll Love These Cookies
- Buttery, soft sugar cookie base
- Sweet, caramelized pineapple topping
- Easy to make with simple ingredients
- Perfect for gatherings and bake sales
- A nostalgic twist on a classic cake
They’re quick to whip up — and even quicker to disappear.
Key Ingredients
For the Cookie Base
Unsalted Butter – Creates a rich, tender texture.
Granulated Sugar – Sweetens and helps create soft cookies.
Egg – Binds everything together.
Vanilla Extract – Adds warm flavor depth.
All-Purpose Flour – Provides structure.
Baking Soda – Gives light lift.
Salt – Balances sweetness.
For the Topping
Pineapple Rings – The star of the show (well-drained for best results).
Extra Sugar – Helps caramelize the pineapple while baking.
How to Make Pineapple Upside Down Sugar Cookies
- Preheat oven to 350°F (180°C) and line baking trays with parchment paper.
- Cream butter and sugar until light and fluffy.
- Mix in egg and vanilla.
- Whisk flour, baking soda, and salt in a separate bowl, then combine with wet ingredients to form a soft dough.
- Scoop about 2 tablespoons of dough per cookie and space evenly on baking trays.
- Press a pineapple ring gently into each dough mound.
- Sprinkle sugar over the pineapple.
- Bake 11–13 minutes until edges are golden.
- Cool slightly before transferring to a wire rack.
Expert Tips
- Use softened butter (not melted) for proper texture.
- Drain pineapple thoroughly to prevent excess moisture.
- Chill dough briefly if cookies spread too much.
- Add a maraschino cherry in the center for a traditional look.
Storage Tips
- Store in an airtight container at room temperature for up to 3 days.
- Freeze baked cookies for up to 2 months.
- Thaw at room temperature or warm slightly in a low oven.
Fun Variations
- Use fresh pineapple slices (thinly cut and patted dry).
- Add shredded coconut to the dough for extra tropical flavor.
- Swap granulated sugar for brown sugar for a caramel undertone.
- Make them dairy-free with plant-based butter.
These Pineapple Upside Down Sugar Cookies bring sunshine to any dessert table. Sweet, buttery, and bursting with tropical flavor, they’re the perfect combination of nostalgia and fun.
Pineapple Upside Down Sugar Cookies
Prep Time: 15 minutes
Bake Time: 11–13 minutes
Yield: 24 cookies
Ingredients
For the Cookie Base
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract (optional)
- 2 cups all-purpose flour (or 1:1 gluten-free blend)
- 1 teaspoon baking soda
- 1/2 teaspoon salt
For the Topping
- 1 can pineapple rings, well-drained
- 2 tablespoons granulated sugar (for sprinkling)
Instructions
- Preheat oven to 350°F (180°C). Line baking trays with parchment paper.
- In a large bowl, cream together butter and sugar until light and fluffy (2–3 minutes).
- Add egg and vanilla extract. Mix until combined.
- In a separate bowl, whisk flour, baking soda, and salt. Gradually add to wet ingredients and mix until a soft dough forms.
- Scoop about 2 tablespoons of dough per cookie and place on prepared trays, spacing them apart.
- Gently press a pineapple ring into each dough mound, flattening slightly.
- Sprinkle sugar over each pineapple ring.
- Bake for 11–13 minutes, until edges are golden and centers are set.
- Cool on the tray for a few minutes, then transfer to a wire rack to cool completely.