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Stack of pineapple upside-down cookies topped with cherries and sugar crystals on a ceramic plate with crumbs

Pineapple Upside-Down Cookies

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These Pineapple Upside-Down Cookies combine the golden caramel flavor of the retro cake with the ease of a handheld cookie. Each bite features a glossy pineapple ring, a sweet cherry center, and a soft, buttery cookie base that melts in your mouth. Perfect for holidays, potlucks, or whenever nostalgia strikes.Ready to bake a crowd-pleasing classic? Try this modern twist on a vintage favorite today!

  • Total Time: 40 minutes
  • Yield: 12 cookies

Ingredients

Scale

Topping Layer:

  • 1/2 cup 1 stick unsalted butter, melted
  • 1/2 cup light brown sugar
  • 6 canned pineapple rings (halved or trimmed to fit molds)
  • 6 maraschino cherries

Cookie Dough:

  • 1 cup 2 sticks unsalted butter, room temperature
  • 1 cup granulated sugar
  • 1/2 cup packed light brown sugar
  • 2 large eggs
  • 1 tsp vanilla extract
  • 1/2 cup sour cream
  • 3 cups all-purpose flour
  • 1 tsp baking powder
  • 1/2 tsp baking soda
  • 1/4 tsp salt
  • 2 tsp cornstarch

Instructions

Step 1: Prepare the Topping

  1. Preheat oven to 350°F (175°C).
  2. Lightly grease or spray a muffin pan.
  3. Pour 1 tsp melted butter and 1 tsp brown sugar into each muffin cup.
  4. Place a halved pineapple ring and one cherry in the center of each.

Step 2: Make the Cookie Dough

  1. In a large bowl, beat softened butter with granulated and brown sugars until fluffy.
  2. Add eggs one at a time, then mix in vanilla and sour cream.
  3. In another bowl, whisk flour, baking powder, baking soda, salt, and cornstarch.
  4. Gradually incorporate the dry mixture into the wet mixture to form a soft dough.

Step 3: Assemble and Bake

  1. Spoon or scoop the cookie dough over the pineapple in each cup, filling almost to the top.
  2. Bake for 18–22 minutes, or until golden and set.
  3. Let cool for 10 minutes, then carefully invert cookies onto a wire rack.

Notes

🧾 Nutrition Information (per cookie)

  • Calories: 190 kcal

  • Fat: 9 g

  • Saturated Fat: 5.5 g

  • Carbohydrates: 26 g

  • Sugar: 16 g

  • Protein: 2 g

  • Fiber: 0.5 g

  • Sodium: 75 mg

  • Prep Time: 20 minutes
  • Cook Time: 20 minutes
  • Category: Cookies, Dessert
  • Cuisine: American