Pineapple Upside Down Cookies

| Posted on:

April 6, 2026

Delicious Pineapple Upside Down Cookies on a plate for dessert

Pineapple Upside Down Cookies offer a fun twist on a classic dessert. With their sweet pineapple topping and cherry centerpiece, they are sure to catch the eye and satisfy a sweet tooth. These cookies are perfect for a casual gathering or as a unique treat to try at home. Easy to make and delightful to eat, they stand out due to their vibrant flavors and playful presentation.

Why cook this at home

Making Pineapple Upside Down Cookies at home allows you to control the ingredients, ensuring freshness and quality. They are a budget-friendly option, as many of the components are pantry staples. The recipe is uncomplicated and versatile, making it an excellent choice for both novice bakers and experienced cooks looking to add a fun dessert to their repertoire. Whether for a weekday treat or a special occasion, these cookies are an engaging way to enjoy the classic flavors of pineapple upside down cake.

Preparing Pineapple Upside Down Cookies

  • Preheat the oven to the correct temperature.
  • Cream together sugar and butter.
  • Create a soft dough by mixing in dry ingredients.
  • Prepare muffin tins with pineapple slices and cherries.
  • Cover the fruit with cookie dough.
  • Bake until golden brown.

Key ingredients

  • 1 cup sugar
  • 1/2 cup butter, softened
  • 1 egg
  • 2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon salt
  • 1/2 cup brown sugar for sprinkling
  • 1 can pineapple slices, drained
  • Maraschino cherries for centers
  • 1/4 cup brown sugar for glaze
  • 1 tablespoon milk

Feel free to substitute with additional fruit if desired, or use alternative sweeteners for a different taste experience.

How to prepare it

  1. Preheat the oven to 350°F (175°C) and prepare a muffin tin.
  2. In a large bowl, cream together the sugar and softened butter until smooth.
  3. Beat in the egg until fully incorporated.
  4. In another bowl, whisk together the flour, baking powder, and salt. Gradually add this mixture to the creamed mixture to form a soft dough.
  5. Place a drained pineapple slice in each muffin cup, press a maraschino cherry into the center, and sprinkle with brown sugar.
  6. Drop spoonfuls of cookie dough over each fruit, covering it.
  7. Bake for 15 to 20 minutes or until golden brown.

Pineapple Upside Down Cookies

What to serve it with

These cookies are best enjoyed warm, with or without a drizzle of glaze. They pair beautifully with a scoop of vanilla ice cream for a delightful contrast in temperature and flavor. A light sprinkle of shredded coconut can also enhance the tropical vibe, making them even more enticing.

How to store and freeze

Store any leftover cookies in an airtight container at room temperature for up to three days. For longer storage, you can freeze them for up to two months. Place layers of parchment paper between the cookies to prevent sticking and thaw overnight in the refrigerator before serving. As with all perishable items, be mindful of the two-hour rule for leaving them out at room temperature to ensure food safety.

Tips for best results

  • Make sure your butter is fully softened for optimal mixing.
  • Use fresh, high-quality pineapple for the best flavor.
  • Do not overmix the cookie dough to keep a soft texture.
  • Allow the cookies to cool slightly before inverting to prevent breakage.
  • Adjust the oven rack to the center for even baking.

Creative twists

  • Substitute the pineapple with peach slices for a different fruit flavor.
  • Add chopped nuts or dried fruit to the cookie dough for a crunchier texture.
  • Experiment with different glazes, such as a honey or maple syrup glaze, to alter the sweetness and taste profile.
  • Use whole wheat flour for a heartier cookie option.

Your questions answered

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple can be used. Just make sure to cut it into even slices and remove any excess moisture.

How can I make these cookies dairy-free?

Replace the butter with a dairy-free alternative, such as coconut oil or a plant-based spread. Use almond milk or another non-dairy milk instead of regular milk.

What is the prep time for these cookies?

The preparation time is about 15-20 minutes, with baking time of 15-20 minutes, making them a quick treat to whip up.

Can I make the dough ahead of time?

Yes, you can prepare the dough in advance and store it in the refrigerator for up to 24 hours before baking. Just allow it to come to room temperature before using it.

How do I know when the cookies are done baking?

The cookies are ready when they turn golden brown around the edges. A toothpick inserted into the cookie should come out clean or with a few moist crumbs.

These Pineapple Upside Down Cookies are a playful take on a classic dessert that combines familiar flavors in an exciting way. Try making them at home, embrace the process, and enjoy the delicious results while sharing your creations with family and friends.

Delicious Pineapple Upside Down Cookies on a plate for dessert

Pineapple Upside Down Cookies

These fun cookies offer a unique twist on the classic pineapple upside down cake, featuring sweet pineapple and a cherry center that make them perfect for casual gatherings or special occasions.
Prep Time 20 minutes
Cook Time 20 minutes
Total Time 40 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American
Calories: 150

Ingredients
  

For the cookie base
  • 1 cup sugar
  • 1/2 cup butter, softened Make sure butter is fully softened for optimal mixing.
  • 1 large egg
  • 2 cups all-purpose flour Can substitute with whole wheat flour for a heartier option.
  • 1 teaspoon baking powder
  • 1/2 teaspoon salt
  • 1/4 cup brown sugar for glaze Add extra brown sugar for sprinkling on top.
  • 1 tablespoon milk Can substitute with a non-dairy alternative.
For the topping
  • 1 can pineapple slices, drained Fresh pineapple can be used instead.
  • Maraschino cherries for centers

Method
 

Preparation
  1. Preheat the oven to 350°F (175°C) and prepare a muffin tin.
  2. In a large bowl, cream together the sugar and softened butter until smooth.
  3. Beat in the egg until fully incorporated.
  4. In another bowl, whisk together the flour, baking powder, and salt. Gradually add this mixture to the creamed mixture to form a soft dough.
Assembling and Baking
  1. Place a drained pineapple slice in each muffin cup, press a maraschino cherry into the center, and sprinkle with brown sugar.
  2. Drop spoonfuls of cookie dough over each fruit, covering it.
  3. Bake for 15 to 20 minutes or until golden brown.

Nutrition

Serving: 1Calories: 150kcalCarbohydrates: 22gProtein: 2gFat: 7gSaturated Fat: 4gSodium: 150mgSugar: 10g

Notes

Best enjoyed warm, with or without a drizzle of glaze. They pair beautifully with vanilla ice cream. Store leftover cookies in an airtight container at room temperature for up to three days or freeze for up to two months.

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