Let’s Bake!
Step 1: Make the Dough
- Cream together softened butter and granulated sugar until light and fluffy (2-3 minutes).
- Beat in the egg and vanilla extract until well combined.
- Whisk together flour, baking soda, and salt. Gradually add to wet ingredients, mixing until just combined. Cover and chill for at least 30 minutes.
Step 2: Caramelize the Pineapple
- Melt 1 tablespoon butter in a skillet over medium heat. Add brown sugar and stir until melted and combined (1-2 minutes).
- Add pineapple rings and cook for about 2 minutes per side, until lightly caramelized. Remove from heat and cool slightly.
Step 3: Assemble & Bake
- Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
- Scoop 1 1/2 tablespoons of chilled dough, roll into a ball, and flatten slightly on the baking sheet.
- Top each cookie with a caramelized pineapple piece and a maraschino cherry half.
- Bake for 12-15 minutes, or until edges are lightly golden.
- Cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
Tips & Tricks
- Chill the dough! This helps the cookies keep their shape.
- Cut large pineapple rings into smaller pieces for easier handling.
- Avoid overbaking to keep cookies soft.
Variations
- Coconut Twist: Add 1/4 cup shredded coconut to the dough.
- Brown Sugar Cookies: Use light brown sugar instead of granulated sugar for a richer flavor.
- Glaze: Drizzle with a powdered sugar glaze for extra sweetness.
Frequently Asked Questions
How do I store them?
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 it 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 before baking.
Can I freeze them?
Yes, freeze baked cookies for up to 2 months. Thaw at room temperature.
Enjoy these delightful Pineapple Upside-Down Sugar Cookies! Happy baking!
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