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Pineapple upside down sugar cookies with caramelized pineapple rings, brown sugar glaze, and bright maraschino cherries cooling on a wire rack

Pineapple Upside Down Sugar Cookies That Delight Every Bite

Thick, soft buttery sugar cookies topped with a brown sugar butter glaze, a caramelized pineapple ring, and a maraschino cherry baked right into the surface. Every element of the classic upside down cake in a handheld cookie that looks impressive and bakes in under 15 minutes.
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Prep Time 20 minutes
Cook Time 14 minutes
Total Time 1 hour 4 minutes
Servings: 14 cookies
Course: Dessert
Cuisine: American
Calories: 324
Ingredients Equipment Method Notes

Ingredients
  

  • 2.5 cups all-purpose flour
  • 3/4 tsp baking powder
  • 1/4 tsp baking soda
  • 1/2 tsp fine salt
  • 1 cup unsalted butter, softened room temperature
  • 3/4 cup granulated sugar
  • 1/4 cup light brown sugar, packed
  • 1 large egg plus 1 egg yolk, room temperature
  • 2 tsp vanilla extract
  • 1 tbsp sour cream or softened cream cheese
  • 1 can (20 oz) pineapple rings in juice, drained and patted very dry
  • 1/4 cup light brown sugar, packed for glaze topping
  • 2 tbsp unsalted butter, melted for glaze topping
  • 1/4 tsp ground cinnamon
  • 14 whole maraschino cherries, stems removed and patted dry

Equipment

  • Stand Mixer with Paddle Attachment
  • Two Baking Sheets lined with Parchment
  • Wire cooling rack
  • Small Bowl for Glaze
  • Paper Towels for Drying Pineapple

Method
 

  1. Whisk flour, baking powder, baking soda, and salt together. Set aside.
  2. Beat butter with both sugars 3 to 4 minutes until fluffy. Add egg and yolk, beat 30 seconds each. Add vanilla and sour cream, mix to combine.
  3. Add flour mixture and mix on low until just combined. Cover and refrigerate dough 30 minutes.
  4. Preheat oven to 350°F. Line baking sheets with parchment. Mix melted butter, brown sugar, and cinnamon for the glaze topping. Scoop dough into 3-tbsp balls, flatten to 3/4 inch thickness on prepared sheets.
  5. Spread a small amount of brown sugar glaze on each disc. Press one dry pineapple ring onto each cookie. Press one dry cherry into the center hole. Spoon remaining glaze over the pineapple.
  6. Bake 12 to 15 minutes until edges are set and very lightly golden. Centers will look slightly underdone. Cool on the pan 10 minutes before transferring to a wire rack.

Notes

  • Pat pineapple rings very dry between paper towels before using - residual juice causes soggy centers and prevents the glaze from setting.
  • Chill dough 30 minutes minimum before baking - this prevents spreading and keeps the cookies thick enough to hold the topping.
  • Do not overbake - edges set but centers looking soft is correct, they firm completely as they cool on the pan.
  • Cool fully on the baking sheet before moving - the glaze needs 10 minutes to set and anchor the pineapple to the cookie surface.
  • Store in a single layer only - stacking transfers moisture from the pineapple onto the cookie below and softens the glaze.