Brown Sugar Glazed Pineapple Upside-Down Cookies

Indulge in soft, buttery pineapple upside-down cookies coated with coarse sugar, caramelized brown sugar glaze, and glossy maraschino cherries. This easy-to-bake dessert delivers classic bakery-style flavors, rich textures, and bright tropical sweetness in every single bite.

Prep time: 20 mins | Bake time: 12 mins | Servings: 12 cookies

Ingredients

For the Cookie Dough

• 1/2 cup unsalted butter, softened

• 1/2 cup granulated sugar

• 1/2 cup light brown sugar, packed

• 1 large egg, room temperature

• 1 tsp vanilla extract

• 2 cups all-purpose flour

• 1/2 tsp baking powder

• 1/4 tsp salt

• 1/3 cup coarse sparkling sugar (for rolling)

For the Pineapple Topping & Glaze

• 12 canned pineapple rings, thoroughly blotted dry

• 12 maraschino cherries, drained and patted dry

• 3 tbsp melted butter

• 1/3 cup dark brown sugar

• 2 tbsp maraschino cherry juice (optional, for drizzling)

Instructions

1. Prep the Oven & Pan

   Preheat your oven to 350°F (175°C) and line two large baking sheets with parchment paper.

2. Mix the Dough

   In a large bowl, cream together the softened butter, granulated sugar, and light brown sugar until light and fluffy. Beat in the egg and vanilla extract until smooth.

3. Combine Dry Ingredients

   Whisk the flour, baking powder, and salt together in a separate bowl. Slowly mix the dry ingredients into the wet mixture until a soft dough forms.

4. Shape & Roll

   Scoop out 12 equal portions of dough (about 2 tablespoons each) and roll them into smooth balls. Roll each dough ball generously in the coarse sparkling sugar to coat the edges, then place them on the prepared baking sheets spaced 2 inches apart. Flatten each ball slightly with your palm.

5. Make the Brown Sugar Glaze

   Whisk the melted butter and dark brown sugar together in a small bowl until completely combined. Spoon a small portion of this glaze over the top of each flattened dough round.

6. Add the Topping

   Press one blotted pineapple ring firmly into the center of each cookie. Place a maraschino cherry right in the middle hole of each pineapple ring. Spoon any remaining brown sugar glaze over the pineapple slices.

7. Bake to Golden Perfection

   Bake for 12 to 14 minutes, until the cookie edges turn light golden brown and the pineapple appears caramelized and glossy.

8. Cool & Serve

   Remove from the oven and let the cookies rest on the baking sheet for 10 minutes to set. Optionally, brush or drizzle a touch of cherry juice over the warm fruit before transferring them to a wire rack to cool completely.