Imagine taking the classic pineapple upside-down cake and transforming it into an irresistible, bite-sized cookie that will make your taste buds dance with joy! These aren't just ordinary cookies - they're a tropical twist on a beloved dessert that combines the sweet, caramelized essence of pineapple with a buttery, soft sugar cookie base. Perfect for summer gatherings, potlucks, or when you simply want to treat yourself to something extraordinary, these cookies are about to become your new obsession.
Prep Time: 15 mins
Cook Time: 10 mins
Total Time: 25 mins
Cuisine: American
Serves: 24 cookies
Ingredients
- 1 cup unsalted butter, softened
- 1 cup sugar
- 2 cups all-purpose flour
- 1 tsp baking powder
- ½ tsp salt
- 1 egg
- 1 tsp vanilla extract
- 1 can pineapple slices, drained
- Maraschino cherries for garnish
Instructions
- Preheat the oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone baking mats.
- In a large mixing bowl, cream together the softened butter and sugar until light and fluffy, using an electric mixer. Beat for approximately 3-4 minutes until the mixture is pale and smooth.
- Add the egg and vanilla extract to the butter mixture. Mix until fully incorporated and the batter is smooth and uniform.
- In a separate bowl, whisk together the all-purpose flour, baking powder, and salt to ensure even distribution of dry ingredients.
- Gradually add the dry ingredient mixture to the wet ingredients, mixing on low speed until just combined. Be careful not to overmix the dough.
- Drain the pineapple slices thoroughly and pat them dry with paper towels to remove excess moisture.
- Cut each pineapple slice into quarters to create smaller pieces that will fit nicely on top of the cookies.
- Scoop rounded tablespoon-sized balls of cookie dough and place them on the prepared baking sheets, leaving about 2 inches of space between each cookie.
- Gently press a pineapple slice quarter onto the top of each cookie dough ball, slightly flattening the dough.
- Place a maraschino cherry in the center of each pineapple slice for added color and flavor.
- Bake in the preheated oven for 10-12 minutes, or until the edges of the cookies are lightly golden brown.
- Remove from the oven and let the cookies cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.
- Once cooled, the cookies can be served immediately or stored in an airtight container at room temperature for up to 5 days.
Tips
- Ensure your butter is truly softened but not melted - this helps create the perfect cookie texture.
- Pat the pineapple slices completely dry to prevent excess moisture from making your cookies soggy.
- Use a cookie scoop for uniform cookie sizes and even baking.
- Don't overbake! The cookies should be just golden at the edges for a soft, tender result.
- Let the cookies cool on the baking sheet for 5 minutes before transferring to prevent breaking.
- For an extra flavor boost, try using brown sugar instead of white sugar for a deeper caramel note.
- Store in an airtight container with a piece of bread to keep them soft and fresh.
Nutrition Facts
Calories: 180kcal
Carbohydrates: 22g
Protein: 2g
Fat: 10g
Saturated Fat: 6g
Cholesterol: 30mg

