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Step-by-Step Instructions

  1. Preheat your oven to 350°F (175°C) and line two baking sheets with parchment paper.
  2. In a large bowl, cream together the softened butter and granulated sugar until light and fluffy, about 3-4 minutes.
  3. Beat in the egg and vanilla extract until well combined.
  4. In a separate bowl, whisk together the flour, baking powder, baking soda, and salt.
  5. Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Be sure not to overmix.
  6. In a small saucepan over medium heat, melt ¼ cup of unsalted butter and the brown sugar until bubbly and well combined.
  7. In each cookie spot on the baking sheet, place a tablespoon of the melted butter-sugar mixture.
  8. Top with a pineapple slice, and place a maraschino cherry in the center of each slice.
  9. Scoop about 1 tablespoon of cookie dough and gently place it over each pineapple slice, pressing down slightly.
  10. Bake for 12-15 minutes or until the edges are lightly golden.
  11. Remove from the oven and let them cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.

Best Ways to Enjoy It

These cookies can stand alone, but why not make them extra special? Serve them warm with a scoop of vanilla ice cream on the side for a delightful dessert experience. Pair them with a tropical fruit salad or a refreshing beverage like iced tea or coconut water to make a summer-themed treat. You could even sprinkle a little toasted coconut on top for added texture and flavor!

How to Store & Freeze

To keep your leftover cookies fresh, store them in an airtight container at room temperature for up to one week. If you want to enjoy them later, consider freezing them. To freeze, place the cookies in a single layer in a freezer-safe container, separating layers with parchment paper. They can be frozen for up to 3 months. When you’re ready to enjoy, just thaw them at room temperature or pop them in the microwave for a few seconds!

Pro Chef Tips

  • Ensure your butter is softened to room temperature for the best creaming results. This helps achieve a fluffy texture in your cookies.
  • Don’t skip the step of draining the pineapple well, or your cookie base can become too soggy.
  • For added flavor, consider adding a pinch of cinnamon or nutmeg to the cookie dough mixture.

Creative Twists

Feeling adventurous? You can easily swap out the pineapple for other fruits like peaches or cherries for a unique take. Want a more tropical vibe? Consider adding shredded coconut or even some crushed macadamia nuts into the cookie dough. For a fun color twist, try different types of cherries, or drizzle some white chocolate over the top before serving.

Common Questions

How long does this recipe take?

From start to finish, you can expect to spend about 30 minutes making these cookies, including preparation and baking time.

Can I use fresh pineapple instead of canned?

Absolutely! Just make sure to cut the fresh pineapple into slices and press out any excess moisture before using.

Are these cookies suitable for freezing?

Yes, they freeze beautifully! Store them in a freezer-safe container for up to 3 months. Just thaw them at room temperature or warm them in the microwave when you’re ready to indulge.

Enjoy making these fun and delicious Pineapple Upside-Down Sugar Cookies—they’re bound to become a new favorite in your home!

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