Pineapple Upside-Down Sugar Cookies

Instructions

Step 1: Prepare the Cookie Dough

1. Cream together softened butter and granulated sugar until light and fluffy (about 2-3 minutes).
2. Beat in the egg and vanilla extract until well combined.
3. Whisk together flour, baking soda, and salt. Gradually add to the wet ingredients, mixing until just combined. Cover and chill for at least 30 minutes.

Step 2: Prepare the Pineapple Topping

1. In a skillet over medium heat, melt 1 tablespoon of butter. Add brown sugar and stir until melted and combined (about 1-2 minutes).
2. Add pineapple rings and cook for about 2 minutes per side, until lightly caramelized. Remove from heat and cool slightly.

Step 3: Assemble the Cookies

1. Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
2. Scoop about 1 1/2 tablespoons of chilled dough, roll into a ball, and flatten slightly on the baking sheet.
3. Top each cookie with a caramelized pineapple piece and a maraschino cherry half.

Step 4: Bake the Cookies

1. Bake for 12-15 minutes, or until edges are lightly golden.
2. Cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

Tips & Notes

• Chill the dough! This helps the cookies keep their shape.
• Cut pineapple rings into smaller pieces if needed.
• Avoid overbaking to keep cookies soft.

Recipe Variations

• Coconut Twist: Add 1/4 cup shredded coconut to the dough.
• Brown Sugar Cookies: Substitute granulated sugar with light brown sugar.
• Glaze: Drizzle with a simple powdered sugar glaze.

Frequently Asked Questions

How do I store these cookies?

Store in an airtight container at room temperature for up to 3 days, or refrigerate for up to 5 days.

Can I use fresh pineapple?

Yes! Cut into small, even pieces and caramelize as directed.

Can I make the dough ahead?

Yes, make and refrigerate the dough for up to 24 hours.

Can I freeze these cookies?

Yes, freeze baked cookies for up to 2 months. Thaw at room temperature.

Enjoy these delightful Pineapple Upside-Down Sugar Cookies! They’re a fun and flavorful treat for any occasion. Happy baking!