Description
Pineapple Upside Down Cookies are a fun twist on the classic cake, featuring a soft, buttery cookie base topped with caramelized pineapple rings and sweet maraschino cherries. With the delicious flavors of brown sugar and vanilla, these cookies are both visually stunning and irresistibly tasty—a perfect dessert or sweet snack for any occasion.
Ingredients
Units
Scale
For the Topping
- 2 (20-ounce) cans pineapple rings, drained
- 9 maraschino cherries, halved
- 1/2 cup brown sugar (about 1 1/2 teaspoons per ring for sprinkling)
For the Cookie Dough
- 1 cup unsalted butter, softened
- 3/4 cup brown sugar
- 1/2 cup granulated sugar
- 2 large eggs
- 1 teaspoon vanilla extract
- 3 cups all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon baking soda
- 1/2 teaspoon salt
Instructions
- Prepare Baking Sheets – Preheat your oven to 400°F (204°C). Line two baking sheets with parchment paper or silicone baking mats to prevent sticking and ensure even baking.
- Prepare Pineapple & Cherries – Drain the juice from the pineapple rings thoroughly and pat dry with paper towels. Arrange the pineapple rings, evenly spaced, on the prepared baking sheets—about 9 per pan. Place a halved maraschino cherry in the center of each pineapple ring, then sprinkle about 1 1/2 teaspoons brown sugar over each ring to create a sweet, caramelized topping.
- Pre-Bake Fruit – Bake the arranged fruit in the oven for about 10 minutes, until the brown sugar is candied onto the pineapple. Remove the trays from the oven and allow them to cool while you prepare the cookie dough.
- Make Cookie Dough – In a large bowl, beat together the softened butter, 3/4 cup brown sugar, and 1/2 cup granulated sugar with a hand mixer for about 3 minutes, until the mixture is pale, smooth, and creamy.
- Add Eggs & Vanilla – Add the eggs and vanilla extract, beating on low speed until just combined, about 30 seconds. Do not overmix.
- Add Dry Ingredients – Gradually add the flour, baking powder, baking soda, and salt to the wet mixture, mixing until just combined. The dough should be soft but workable.
- Form and Assemble Cookies – Take about 2 tablespoons of the cookie dough and form a ball. Place each dough ball atop the candied pineapple rings on the baking sheets, and gently press down to slightly flatten the dough so it adheres to the ring and covers the fruit.
- Bake Cookies – Return the pans to the oven and bake for 12-14 minutes, or until the tops of the cookies are golden brown. The edges should be set, and the cookies will be just cooked through.
- Cool and Serve – Let the cookies cool on the baking sheets for at least 15 minutes before serving warm, or carefully transfer them to a wire rack to cool completely if desired. Enjoy!
Notes
- The fruit means these cookies require refrigeration. Store them in an airtight container or plastic bag in the refrigerator for up to 5 days.
- Patting the pineapple rings dry helps prevent excess moisture, ensuring the cookies do not become soggy.
- Allow cookies to cool on the sheet to minimize breaking, as they will be delicate when warm.
Nutrition
- Serving Size: 1 cookie
- Calories: 245
- Sugar: 22g
- Sodium: 198mg
- Fat: 10g
- Saturated Fat: 6g
- Unsaturated Fat: 4g
- Trans Fat: 0.4g
- Carbohydrates: 37g
- Fiber: 1g
- Protein: 3g
- Cholesterol: 43mg
