These Pineapple Upside‑Down Sugar Cookies are a fun mashup of two favorite desserts. A buttery sugar cookie base is baked right over sweet pineapple slices and maraschino cherries, then flipped to reveal a caramelized fruit topping. They look stunning, taste amazing, and bring tropical vibes to every bite.
Why I’ll Love This Recipe
I love this recipe because it transforms two nostalgic desserts into one beautiful treat. The soft sugar cookie dough balances perfectly with the caramelized pineapple and cherry topping. It’s easy to make, uses simple ingredients, and the results always impress. I also like how portable these are — they’re perfect for sharing at parties or baking for someone special.
Ingredients
(Here’s a tip: Check out the full list of ingredients and measurements in the recipe card below.)
For the topping
½ cup unsalted butter, melted
1 cup light brown sugar, packed
Pineapple slices (canned or fresh, well-drained)
Maraschino cherries
For the sugar cookie dough
1 cup unsalted butter, softened
1½ cups granulated sugar
2 large eggs
½ cup sour cream
3 cups all-purpose flour
1 teaspoon baking powder
1 teaspoon cornstarch
½ teaspoon salt
2 teaspoons vanilla extract
Directions
Preheat the oven to 350°F (175°C).
Grease a muffin tin or line it with parchment rounds.
In a small bowl, mix the melted butter and brown sugar. Add about a tablespoon of the mixture to the bottom of each muffin cup.
Place a pineapple slice over the brown sugar layer. Add a maraschino cherry in the center of each pineapple ring.
In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
Add the eggs one at a time, beating after each addition. Mix in the sour cream and vanilla.
In a separate bowl, whisk together the flour, baking powder, cornstarch, and salt.
Gradually add the dry ingredients to the wet mixture, stirring just until combined.
Scoop about 2 tablespoons of dough, flatten slightly, and press it over the top of the fruit in each muffin cup.
Bake for 12 to 15 minutes, or until the edges of the cookies are just turning golden.
Let the cookies cool in the pan for 10 minutes.
Carefully invert the muffin tin onto a cooling rack or parchment paper to release the cookies with the fruit side up.
Allow them to cool completely before serving.
Servings and timing
Servings: 12 to 14 cookies
Prep time: 20 minutes
Bake time: 12–15 minutes
Total time: About 40 minutes
Variations
Use fresh pineapple slices for a bolder flavor.
Swap sour cream for plain yogurt in the dough.
Add a dash of cinnamon or ginger to the cookie dough for warmth.
Try chopped pineapple instead of slices for a different look and texture.
Drizzle with white chocolate after cooling for a sweeter finish.
Storage / reheating
I store these cookies in an airtight container at room temperature for up to 3 days.
If I want to keep them longer, I refrigerate them — just make sure to bring them to room temperature before serving.
To reheat, I place them in a warm oven (around 300°F) for 3–5 minutes to revive the softness.
I don’t recommend freezing them once baked, because the pineapple can release too much moisture during thawing.
FAQs
Can I use crushed pineapple instead of slices?
Yes, but I make sure to drain it really well. I just spoon some crushed pineapple into the muffin cups with the cherry and brown sugar.
What if the cookies don’t come out cleanly when flipped?
I let them cool for 10 minutes in the pan, then run a knife around the edge before flipping. If they stick a bit, I gently lift them out and reshape while warm.
Can I make these without sour cream?
Yes — I replace it with plain yogurt or even buttermilk. The dough stays soft and tender.
Do I have to use a muffin tin?
It helps with shaping and holding the pineapple in place, but I’ve also used ramekins or silicone molds with good results.
Can I prepare the dough in advance?
Absolutely. I chill the dough up to 24 hours ahead, then bring it slightly to room temperature before assembling and baking.
Conclusion
These Pineapple Upside‑Down Sugar Cookies are as beautiful as they are delicious. I love how the sweet fruit topping caramelizes into the soft sugar cookie base. They’re tropical, fun, and always a crowd favorite. Whether I bake them for a party or just for myself, they never last long.
These Pineapple Upside-Down Sugar Cookies combine the charm of classic pineapple upside-down cake with buttery sugar cookies. Each cookie features caramelized pineapple and a cherry topping baked beneath a soft, tender cookie base for a tropical treat that’s as beautiful as it is delicious.
Total Time:40 minutes
Yield:12–14 cookies
Ingredients
½ cup unsalted butter, melted
1 cup light brown sugar, packed
Pineapple slices (canned or fresh, well-drained)
Maraschino cherries
1 cup unsalted butter, softened
1½ cups granulated sugar
2 large eggs
½ cup sour cream
3 cups all-purpose flour
1 teaspoon baking powder
1 teaspoon cornstarch
½ teaspoon salt
2 teaspoons vanilla extract
Instructions
Preheat oven to 350°F (175°C). Grease a muffin tin or line it with parchment rounds.
In a small bowl, combine melted butter and brown sugar. Spoon about 1 tablespoon into each muffin cup.
Place a pineapple slice on top of the brown sugar mixture, and add a maraschino cherry in the center.
In a large bowl, cream softened butter and granulated sugar until light and fluffy.
Add eggs one at a time, mixing well after each addition. Stir in sour cream and vanilla extract.
In a separate bowl, whisk together flour, baking powder, cornstarch, and salt.
Gradually add dry ingredients to the wet mixture, mixing just until combined.
Scoop about 2 tablespoons of dough, flatten slightly, and press it over the fruit layer in each muffin cup.
Bake for 12–15 minutes, or until edges are lightly golden.
Cool in the pan for 10 minutes, then carefully invert the tin onto a cooling rack or parchment paper to release the cookies fruit-side up.
Let cool completely before serving.
Notes
Use fresh pineapple for a bolder flavor and less sweetness.
Substitute sour cream with plain yogurt or buttermilk if needed.
Add cinnamon or ginger to the dough for extra warmth.
Try chopped pineapple for a different look and texture.
Drizzle with melted white chocolate once cooled for a sweet finish.
Cool for 10 minutes before flipping to prevent breakage.
