I take everything I love about classic pineapple upside down cake and turn it into soft, buttery sugar cookies. I top each cookie with caramelized brown sugar, juicy pineapple, and a bright cherry center. They come out sweet, slightly tangy, and beautifully golden on top.
Why You’ll Love This Recipe
I love how these cookies combine the nostalgic flavor of pineapple upside down cake with the simplicity of a sugar cookie. I get a soft and tender texture from the cookie base, while the pineapple topping adds a juicy contrast. I also appreciate how eye-catching they look with their caramelized tops and bright cherry centers. I find them perfect for parties, holidays, or whenever I want something a little different from traditional cookies.
Ingredients
(Here’s a tip: Check out the full list of ingredients and measurements in the recipe card below.)
For the topping:
1/4 cup unsalted butter, melted 1/2 cup packed light brown sugar 6 pineapple rings, cut into small pieces 6 maraschino cherries, halved
For the sugar cookies:
1/2 cup unsalted butter, softened 3/4 cup granulated sugar 1 large egg 1 teaspoon vanilla extract 1 1/2 cups all-purpose flour 1/2 teaspoon baking powder 1/4 teaspoon baking soda 1/4 teaspoon salt
Directions
I preheat my oven to 350°F (175°C) and lightly grease a muffin tin or line it with parchment liners to help the cookies release easily.
I spoon a small amount of melted butter into each muffin cavity, then sprinkle brown sugar evenly over the butter.
I place a few small pieces of pineapple into each cavity and press a cherry half into the center. I set the pan aside while I prepare the dough.
In a mixing bowl, I cream the softened butter and granulated sugar together until light and fluffy.
I mix in the egg and vanilla extract until fully combined.
In a separate bowl, I whisk together the flour, baking powder, baking soda, and salt. I gradually add the dry ingredients to the wet mixture and stir just until a soft dough forms.
I scoop the dough over the pineapple topping in each muffin cavity, gently spreading it to cover the fruit.
I bake for 18–22 minutes, or until the edges are lightly golden and the centers are set.
I let the cookies cool in the pan for about 5 minutes, then carefully invert them onto a baking sheet or wire rack so the pineapple topping is on top. I allow them to cool completely before serving.
Servings and timing
I make about 12 cookies from this recipe.
Prep time: 15 minutes Bake time: 18–22 minutes Total time: About 40 minutes
Variations
I sometimes add a splash of pineapple juice to the cookie dough for extra flavor. When I want a tropical twist, I mix in a tablespoon of shredded coconut. If I feel like experimenting, I swap the vanilla extract for coconut extract. I also like to add a pinch of cinnamon to the brown sugar layer for a warm, spiced version.
storage/reheating
I store these cookies in an airtight container in the refrigerator for up to 3 days because of the fruit topping. Before serving, I let them sit at room temperature for about 15–20 minutes. If I want them slightly warm, I heat them in the microwave for about 10 seconds, just enough to soften the caramelized topping without making them soggy.
FAQs
Can I use canned pineapple?
I use canned pineapple rings most of the time, and I make sure to drain them well and pat them dry so the cookies do not become too moist.
Can I make these cookies without a muffin tin?
I prefer using a muffin tin to hold the topping in place, but if I do not have one, I shape small wells in a baking sheet lined with parchment and carefully assemble the topping inside each one.
How do I prevent the cookies from sticking?
I grease the pan well and do not skip the step of inverting them while they are still slightly warm. That helps release the caramelized sugar before it hardens.
Can I freeze these cookies?
I freeze them without the topping when possible. If I freeze them fully assembled, I wrap them tightly and thaw them in the refrigerator before serving.
Why are my cookies too soft?
If my cookies turn out too soft, I usually find that I underbaked them slightly or added too much pineapple. I make sure to measure carefully and bake until the edges are lightly golden.
Conclusion
I love how these pineapple upside down sugar cookies bring a classic dessert flavor into a fun, handheld treat. I get a soft sugar cookie base with a caramelized pineapple topping that looks as good as it tastes. Whenever I want a dessert that stands out on the table, I turn to this recipe and enjoy every sweet, fruity bite.
Soft and buttery sugar cookies topped with caramelized brown sugar, juicy pineapple pieces, and bright cherry centers, inspired by classic pineapple upside down cake.
Ingredients
1/4 cup unsalted butter, melted
1/2 cup packed light brown sugar
6 pineapple rings, cut into small pieces
6 maraschino cherries, halved
1/2 cup unsalted butter, softened
3/4 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
1 1/2 cups all-purpose flour
1/2 teaspoon baking powder
1/4 teaspoon baking soda
1/4 teaspoon salt
Instructions
Preheat the oven to 350°F (175°C) and lightly grease a muffin tin or line with parchment liners.
Spoon a small amount of melted butter into each muffin cavity and sprinkle brown sugar evenly over the butter.
Add small pieces of pineapple into each cavity and press a cherry half into the center. Set aside.
In a mixing bowl, cream the softened butter and granulated sugar together until light and fluffy.
Mix in the egg and vanilla extract until fully combined.
In a separate bowl, whisk together flour, baking powder, baking soda, and salt. Gradually add the dry ingredients to the wet mixture and stir just until a soft dough forms.
Scoop the dough over the pineapple topping in each muffin cavity, gently spreading it to cover the fruit.
Bake for 18–22 minutes, or until the edges are lightly golden and centers are set.
Cool in the pan for 5 minutes, then carefully invert onto a baking sheet or wire rack. Allow to cool completely before serving.
Notes
Drain and pat pineapple dry to prevent excess moisture.
Invert cookies while slightly warm to prevent sticking.
Store in an airtight container in the refrigerator for up to 3 days.
Let cookies sit at room temperature 15–20 minutes before serving.
