Easy Pineapple Upside-Down Cupcakes

Satisfy your sweet cravings without derailing your wellness journey with the indulgent yet figure-friendly  Low-Points Pineapple Upside-Down Cupcakes. This clever twist on the classic dessert transforms the tropical allure of pineapple and the sweetness of brown sugar into a portion-controlled delight that aligns with your  plan.

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Beginning with a pineapple topping that undergoes a delightful caramelization process, these cupcakes bring a burst of fruity sweetness to each bite. The meticulous balance of ingredients, including sugar substitutes and carefully measured portions, keeps the point count low while ensuring a rich and satisfying flavor profile.

The cupcake batter, crafted with precision, features a blend of flour, sugar substitute, baking powder, and a hint of salt. Wet ingredients such as applesauce, vegetable oil, eggs, vanilla extract, and a touch of milk come together to create a moist and flavorful base. Spooned over the caramelized pineapple in each cupcake liner, the batter bakes into a golden perfection, ready to be enjoyed guilt-free.

These cupcakes not only deliver on taste but also on mindful eating. The portion-controlled servings make them a perfect treat for those adhering to  points, allowing for a moment of sweet indulgence without compromising on health-conscious choices.

Whether you’re treating yourself to a guilt-free dessert or sharing these delightful cupcakes at gatherings, they are sure to captivate taste buds and prove that wholesome ingredients and mindful portions can coexist in a delicious harmony. The  Low-Points Pineapple Upside-Down Cupcakes offer a delectable solution for those seeking a healthier twist on a classic favorite—a celebration of flavor, balance, and smart choices.


For the Pineapple Upside-Down Topping:

  • 1 can (20 oz) pineapple slices in juice (reserve juice)
  • 6 maraschino cherries, halved

For the Cupcake Batter:

  • 1 cup all-purpose flour
  • 1/2 cup granulated sugar or sugar substitute
  • 1/4 cup unsweetened applesauce
  • 1/4 cup plain non-fat Greek yogurt
  • 1/4 cup reserved pineapple juice
  • 1 large egg
  • 1 teaspoon baking powder
  • 1/2 teaspoon vanilla extract
  • Pinch of salt


  1. Preheat your oven to 350°F (175°C). Line a muffin tin with paper cupcake liners.
  2. For the Pineapple Upside-Down Topping: Drain the pineapple slices and reserve 1/4 cup of the juice. Place a pineapple slice in the bottom of each cupcake liner and add half of a maraschino cherry in the center of each pineapple slice.
  3. For the Cupcake Batter: In a bowl, whisk together flour, sugar or sugar substitute, baking powder, and a pinch of salt.
  4. In another bowl, mix together applesauce, Greek yogurt, reserved pineapple juice, egg, and vanilla extract.
  5. Combine the wet and dry ingredients, stirring until just combined.
  6. Spoon the batter evenly over the pineapple slices in the cupcake liners.
  7. Bake in the preheated oven for about 18-20 minutes or until a toothpick inserted into the center comes out clean.
  8. Allow the cupcakes to cool in the tin for a few minutes before transferring them to a wire rack to cool completely.
  9. Optionally, garnish with additional pineapple slices and cherries.
  10. Serve and enjoy!

Nutritional Information (approximate per cupcake, assuming 12 cupcakes):

Calories: Approximately 90

Protein: 2g

Carbohydrates: 20g

Dietary Fiber: 1g

Sugars: 11g

Fat: 1g

Saturated Fat: 0g

Cholesterol: 15mg

Sodium: 70mg

 Points (approximate):

  • This recipe is generally considered to be around 2 SmartPoints per cupcake, but please double-check with the specific ingredients you use and the current  plan you’re following.

Note: Nutritional values and points are approximate and may vary based on specific ingredients and brands used. Adjust the ingredients to meet your dietary preferences and needs.

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