Pineapple Upside Down Sugar Cookies (Print View)

Soft sugar cookies with brown sugar glaze, pineapple, and cherries—perfect for a sweet tropical touch.

# Components:

→ Cookie Dough

01 - 1 cup unsalted butter, at room temperature
02 - 1 1/2 cups granulated sugar
03 - 2 large eggs
04 - 2 teaspoons vanilla extract
05 - 1/2 cup sour cream
06 - 3 cups all-purpose flour
07 - 1 teaspoon baking powder
08 - 1 teaspoon cornstarch
09 - 1/2 teaspoon salt

→ Toppings

10 - 13 canned pineapple slices, drained
11 - 13 maraschino cherries
12 - 1/2 cup unsalted butter, melted
13 - 1 cup light brown sugar, packed

# Directions:

01 - Preheat oven to 350°F (175°C). Grease a mini round cake pan or muffin tin.
02 - In a large mixing bowl, cream together room temperature butter and granulated sugar with an electric mixer until light and fluffy.
03 - Add eggs, vanilla extract, and sour cream to the creamed mixture. Mix until fully integrated.
04 - In a separate bowl, whisk together all-purpose flour, baking powder, cornstarch, and salt.
05 - Gradually add dry ingredients into the wet mixture, mixing until just combined. Set dough aside.
06 - In another bowl, blend melted butter and light brown sugar until smooth.
07 - Spoon about 1 tablespoon of the brown sugar mixture into each cavity of the prepared pan, spreading evenly.
08 - Place a pineapple slice over the brown sugar glaze. Position a maraschino cherry in the center of each pineapple ring.
09 - Using a 3-tablespoon scoop, portion cookie dough over each fruit-topped cavity. Gently flatten the dough with an offset spatula.
10 - Bake for 25 minutes, or until the cookies are golden around the edges and the brown sugar is bubbling up the sides.
11 - Cool for 10 minutes, then carefully invert cookies onto wax paper to allow brown sugar glaze to run over the tops.
12 - Allow cookies to cool completely before serving. Store in an airtight container.

# Expert Advice:

01 -
  • Uses straightforward pantry and fridge staples with a fun fruity twist
  • Ready in under an hour including cooling time
  • Each bite offers the nostalgia of classic pineapple upside down cake in a hand-held form
02 -
  • Vegetarian friendly
  • Texture is extra soft for several days
  • Dough holds shape bright and tall in a muffin tin
  • Light brown sugar is my favorite here because it never overwhelms the pineapple. I will never forget the first time I flipped the cookies over and saw the caramel bubbling with fruit — the kitchen filled with the happiest scent.
03 -
  • Pat pineapple slices dry with paper towels to avoid extra bubbling during baking
  • Use an offset spatula for easy dough spreading and to keep fruit visible
  • Let the cookies rest ten minutes before unmolding to keep the syrup thick and sticky for the best gooey effect

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