Pineapple Upside Down Sugar Cookies

These delightful cookies capture all the flavors of classic pineapple upside down cake in portable cookie form! With a buttery sugar cookie base, caramelized pineapple topping, and maraschino cherries, they’re sure to be a hit.

Ingredients

For the Topping:

• 6 maraschino cherries, halved

• 6 pineapple rings (canned), patted dry and each cut into 6 wedges

• ¼ cup unsalted butter

• ½ cup packed light brown sugar

• 1 tablespoon pineapple juice (from the can)

For the Cookie Dough:

• 2¾ cups all-purpose flour

• 1 teaspoon baking soda

• ½ teaspoon baking powder

• ½ teaspoon salt

• 1 cup unsalted butter, softened

• 1½ cups granulated sugar

• 1 large egg

• 1 teaspoon vanilla extract

• ¼ cup sour cream

Instructions

Step 1: Prepare the Topping

1. Melt ¼ cup butter in a small saucepan over medium heat.

2. Stir in brown sugar and pineapple juice until sugar dissolves and mixture is bubbly (about 2-3 minutes).

3. Remove from heat and let cool slightly while preparing pans.

Step 2: Assemble Topping in Pans

1. Line two baking sheets with parchment paper.

2. Spoon about 1 teaspoon of the caramel mixture into 12 evenly spaced mounds on each sheet (24 total).

3. Place 3 pineapple wedges in a pinwheel pattern on each caramel mound.

4. Place a cherry half in the center of each pineapple arrangement.

Step 3: Make the Cookie Dough

1. In a medium bowl, whisk together flour, baking soda, baking powder, and salt.

2. In a large bowl, beat softened butter and granulated sugar until light and fluffy (2-3 minutes).

3. Beat in egg and vanilla until combined.

4. Mix in sour cream.

5. Gradually add dry ingredients to wet ingredients, mixing until just combined.

Step 4: Assemble and Bake

1. Scoop about 2 tablespoons of dough (or use a medium cookie scoop) and place directly over each pineapple arrangement, covering completely.

2. Chill prepared cookies for 30 minutes (this prevents excessive spreading).

3. Preheat oven to 350°F (175°C).

4. Bake for 12-14 minutes, until edges are golden brown.

5. Let cool on baking sheets for 5 minutes only.

Step 5: Flip the Cookies

1. While still warm, carefully flip each cookie onto a cooling rack or plate.

2. If any pineapple sticks to the parchment, gently remove and place back on the cookie.

3. Allow to cool completely before serving.

Tips for Success

• Pat pineapple dry thoroughly to prevent soggy cookies

• Don’t overbake – cookies continue to set as they cool

• Flip while warm but not hot for best results

• Use quality pineapple – it’s the star flavor!

Storage

Store in an airtight container at room temperature for up to 4 days. Separate layers with parchment paper to prevent sticking.

Enjoy these tropical treats that bring vacation vibes to your cookie jar!