Description
These Pineapple Upside Down Cookies combine the classic tropical flavors of pineapple and maraschino cherries with a buttery, soft cookie base. Featuring a delightful brown sugar butter topping, these cookies are baked upside down for a visually stunning presentation and a rich, caramelized taste.
Ingredients
Scale
Topping
- 6 tablespoons Butter, melted
- 1 cup Brown Sugar (214g)
- Pineapple Rings, drained
- Maraschino Cherries, drained
Cookie Dough
- ½ cup Butter, softened
- ½ cup Granulated Sugar (100g)
- 1 Egg, large
- 1 teaspoon Vanilla Extract
- ½ cup Powdered Sugar (65g)
- ¼ cup Vegetable Oil
- ½ teaspoon Baking Soda
- ½ teaspoon Cream of Tartar
- 2 cups All Purpose Flour (240g)
Instructions
- Pan Preparations: Preheat your oven to 350°F (175°C). In a smaller mixing bowl, combine 6 tablespoons of melted butter with 1 cup of brown sugar and mix until smooth. Drain the pineapple rings and maraschino cherries thoroughly to prevent excess moisture.
- Arrange Toppings: Place about 1 tablespoon of the brown sugar butter mixture into each well of your muffin tin. Press one pineapple ring into the mixture, then place one maraschino cherry in the center of the pineapple ring. Stagger the positions of the toppings to allow cookies room to spread without touching.
- Make Cookie Dough: In a mixing bowl, cream together softened butter and granulated sugar until light and fluffy, scraping the sides as needed. Add the egg and vanilla extract, continuing to cream for 2 to 3 minutes until well combined.
- Incorporate Wet Ingredients: Gradually add the vegetable oil and powdered sugar to the butter mixture, beating until pale yellow and thoroughly combined.
- Add Dry Ingredients: Sift together the all-purpose flour, baking soda, and cream of tartar. Gradually add these dry ingredients to the wet mixture, mixing until fully incorporated into a cookie dough.
- Shape Cookies: Using a #24 cookie scoop, portion the dough into balls. Flatten each ball with your palm to about 3 inches in diameter.
- Assemble Cookies: Place each flattened cookie dough piece on top of the pineapple ring and cherry in the muffin tin wells. Carefully tuck and press the dough into the sides of each well, sealing the edges to encase the fruit and sugar mixture.
- Bake: Bake the cookies at 350°F for 8 to 10 minutes, or until the edges are lightly golden and the centers are no longer glossy.
- Invert Cookies: Remove the muffin tin from the oven and immediately invert the pan onto a parchment-lined baking sheet. The cookies will fall out, revealing the classic pineapple upside down topping on top.
- Cool and Serve: Allow the cookies to cool completely before serving to let the caramelized topping set for the best flavor and texture experience.
Notes
- Make sure to drain pineapple rings and maraschino cherries very well to prevent soggy cookies.
- Use a non-stick muffin tin or lightly grease the pan to help cookies release easily after baking.
- Stagger cookie placement in the pan to avoid merging during baking.
- If desired, substitute vegetable oil with melted coconut oil for a subtle tropical flavor twist.
- Store cooled cookies in an airtight container at room temperature for up to 4 days.
- Prep Time: 20 minutes
- Cook Time: 10 minutes
- Category: Dessert, Cookies
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 190 kcal
- Sugar: 15 g
- Sodium: 65 mg
- Fat: 9 g
- Saturated Fat: 3.5 g
- Unsaturated Fat: 4.5 g
- Trans Fat: 0 g
- Carbohydrates: 26 g
- Fiber: 1 g
- Protein: 2 g
- Cholesterol: 30 mg
Keywords: pineapple upside down cookies, pineapple cookies, upside down dessert, tropical cookies, pineapple cherry cookies
