Weight Watchers Pineapple Upside Down Cupcakes

These Weight Watchers Pineapple Upside Down Cupcakes are a light cupcake version of the popular cake where pineapple and cherries are cooked in the bottom of a pan! Easy to make, fun to look at, and yummy to eat-which makes for a fantastic snack or dessert!


PREP TIME10 minutes

COOK TIME20 minutes


TOTAL TIME40 minutes


  • 1 box (16 oz.) Pillsbury sugar free yellow cake mix 
  • 1 cup water  
  • 3 eggs 
  • 1/3 cup unsweetened applesauce  
  • 1 tsp vanilla extract 
  • 1 Tbsp light butter made with canola oil or any light butter, melted  
  • 3 Tbsp zero point brown sugar sweetener ( Lakanto Golden Monkfruit Sweetener) or regular brown sugarh
  • 1 can (16 oz.) pineapple chunks in 100% juice, drained 
  • 16 maraschino cherries, halved 
  • Fat free cool whip and maraschino cherries, optional for garnish 


  1. Preheat oven to 350 degrees.
  2. Spray 16 muffin cups with no-stick cooking spray. Set aside.
  3. In a large mixing bowl combine sugar free cake mix, water, eggs, unsweetened applesauce, and vanilla extract. Whisk until blended.
  4. Combine melted light butter with regular brown sugar sweetener in a small bowl. Stir until smooth. 
  5. Spoon about 1 tsp of the sugar mixture into each prepared muffin cup. 
  6. Top with 3-4 chunks of pineapple and 1/2 cherry in the middle of the pineapple chunks. 
  7. Evenly fill each muffin cups with cake batter.
  8. Bake 20 minutes or until a toothpick inserted into center of cupcakes comes out clean. 
  9. Let them cool for 10-15 minutes before gently flipping them over onto a clean surface. 
  10. Top each cupcake with cool whip and a cherry for an additional point, if desired.

Makes 16 cupcakes 
4 Points® per cupcake


  • Store leftover cupcakes without cool whip in an airtight container in the fridge for up to a week or freezer for up to a month. Thaw overnight in the fridge. 
  • Nutrition Information:
  • YIELD: 16 

By Chochi

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