These Pineapple Upside-Down Cookies transform the classic cake into perfectly portable treats that capture all those beloved tropical flavors. Each soft, buttery cookie is crowned with a juicy pineapple chunk and a bright maraschino cherry, creating that signature upside-down cake look in cookie form. They’re perfect for parties, picnics, or whenever you want a taste of sunshine.
If you love these fruity flavors, you’ll adore our Hawaiian Banana Bread with Coconut & Pineapple for another tropical treat. For more cookie perfection, try our Strawberry & Lemon Blondies—they offer that same bright, fruity sweetness that makes these pineapple cookies so special.
Pineapple Upside-Down Cookies
Pineapple Upside-Down Cookies bring the beloved flavors of the iconic cake into bite-sized treats with tender, buttery cookies topped with juicy pineapple chunks and sweet maraschino cherries.
4
servings30
minutes40
minutes300
kcal1
hour10
minutesIngredients
1 cup all-purpose flour
1/2 teaspoon baking powder
1/4 teaspoon baking soda
1/4 teaspoon salt
1 stick butter, softened
1/2 cup granulated sugar
1 large egg
1 tablespoon pineapple juice
1 cup pineapple chunks
24 maraschino cherries
Directions
- Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper to prevent sticking.
- In a bowl, whisk together the flour, baking powder, baking soda, and salt to combine the dry ingredients thoroughly.
- In a separate bowl, cream together the softened butter and granulated sugar until light and fluffy using an electric mixer.
- Beat in the egg and pineapple juice into the sugar and butter mixture until well incorporated and smooth.
- Gradually add the dry ingredients to the wet mixture, mixing until just combined to form a smooth cookie dough.
- Scoop about a tablespoon of dough for each cookie and place it on the prepared baking sheet with some space between each.
- Press a pineapple chunk into the center of each cookie, followed by a maraschino cherry on top, pressing lightly.
- Bake in the preheated oven for about 12 to 15 minutes until edges are golden brown, then allow to cool on a wire rack.
Nutrition Facts
- Total number of serves: 4
- Calories: 250kcal
- Cholesterol: 0mg
- Sodium: 620mg
- Potassium: 400mg
- Sugar: 8g
- Protein: 6g
- Calcium: 60mg
- Iron: 2mg
Can’t get enough of great flavors? Check out these popular recipes that readers love making again and again.
For tropical-inspired treats, our Mini Pineapple Upside-Down Cheesecakes and Coconut Cream Bars bring that same sweet, fruity satisfaction. When you’re craving more cookie varieties, the Espresso Toffee Cookies and Blueberry Cheesecake Cookies deliver irresistible flavors in every bite. Need crowd-pleasing desserts? Our No-Bake Chocolate Eclair Cake and Cheesecake Brownies are always hit at gatherings.
Browse our full collection for more kitchen inspiration that’ll have your family asking for seconds.
