Take the classic pineapple upside-down cake and shrink it into a bite-sized, sweet, and tropical cookie. These Pineapple Upside Down Sugar Cookies combine the soft, buttery goodness of a sugar cookie with the rich, caramelized flavor of pineapple and brown sugar. The addition of maraschino cherries creates the perfect visual pop, making them ideal for summer gatherings, holiday baking, or just a fun treat for the whole family.

Unlike traditional pineapple upside-down cakes, these cookies are quick to bake, individually portioned, and perfectly shareable. Each cookie is soft on the inside, slightly crisp on the edges, and bursting with the tropical flavor that makes pineapple desserts so irresistible.

Ingredients

Cookie Base

2 ½ cups all-purpose flour
1 tsp baking powder
½ tsp salt
¾ cup unsalted butter, softened
1 cup granulated sugar
2 large eggs
2 tsp vanilla extract

Topping

½ cup brown sugar, packed
4 tbsp unsalted butter, melted
½ cup pineapple chunks (fresh or canned)
12 maraschino cherries, halved

Instructions

Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
Mix dry ingredients: In a medium bowl, whisk together flour, baking powder, and salt.
Cream butter and sugar: In a large bowl, beat butter and granulated sugar until fluffy. Add eggs one at a time, mixing well, then stir in vanilla extract.
Combine dry and wet ingredients: Gradually add the flour mixture until a soft dough forms.
Prepare topping: In a small bowl, combine brown sugar and melted butter.
Shape cookies: Roll dough into 1.5-inch balls. Flatten slightly and place on baking sheet. Press a small amount of brown sugar mixture onto the top of each cookie.
Add pineapple and cherry: Place a small pineapple chunk and half a maraschino cherry on each cookie. Press gently so toppings adhere.
Bake: Bake 12–15 minutes, or until edges are lightly golden.
Cool: Allow cookies to cool on the baking sheet for 5 minutes, then transfer to a wire rack. Serve warm or room temperature.

Tips for Perfect Pineapple Upside Down Cookies

Drain pineapple well: If using canned pineapple, drain excess juice to prevent soggy cookies.
Even topping: Use a small spoon to evenly distribute brown sugar mixture for consistent caramelization.
Storage: Store in an airtight container for up to 3 days.

Variations

Mini version: Make bite-sized cookies for party platters.
Tropical twist: Add a few shredded coconut flakes to the dough.
Spiced flavor: Mix ¼ tsp cinnamon or nutmeg into the cookie dough for added warmth.

Serving Suggestions

Pair with a tropical iced tea or milk for a fun snack.
Arrange on a decorative platter for summer parties.
Great as a gift: wrap a few cookies in a small box with ribbon for a festive treat.

Fun Facts

Pineapple upside-down cake dates back to the early 20th century in the United States.
Transforming it into cookies allows the flavors to shine in a quick, portable dessert.
Caramelized pineapple topping adds a sweet, tangy contrast to the buttery cookie base.