
If you’re a fan of classic desserts and looking for a healthier option, this Weight Watchers Pineapple Upside Down Cake is for you! By using zero-calorie sweetener and maple syrup, this recipe keeps the points low without sacrificing the delicious caramelized flavor you love. The combination of soft, tender cake and the rich, fruity topping is sure to satisfy your sweet tooth while keeping you on track with your goals. Decorated with vibrant pineapple rings and maraschino cherries, this cake not only tastes great but also looks stunning. Save this easy recipe to enjoy a guilt-free treat that everyone will rave about!

Pineapple Upside Down Cake Ingredients
Cake Batter
- ¾ cup Zero-calorie sweetener (use a cup-for-cup replacement like monk fruit sweetener with erythritol)
- 1 Egg
- 1 tsp Vanilla extract
- ⅓ cup Canola oil
- ½ cup Unsweetened almond milk
- 1 ¼ cup All-purpose flour
- 1 ¼ tsp Baking powder
- 1 tbsp 0% Greek yogurt
- Salt (just a pinch
Pineapple Base
- 3 tbsp Sugar-free maple syrup (or pure maple syrup, which raises it to 5 WW points)
- 1 tsp Cinnamon
- 6 Sliced pineapple rings (drained)
- 6 Maraschino cherries (stems removed, drained)

How to Make WW Pineapple Upside Down Cake (Step by Step)
Step into a world of sweet indulgence with this step-by-step guide to crafting a Weight Watchers Pineapple Upside Down Cake. From caramelized pineapple slices to a fluffy, guilt-free cake base, each layer is a symphony of flavor and health-conscious delight, making every bite a joyous celebration of balanced eating.

Preheat Oven
Preheat the oven to 350°F.

Drain Pineapple and Cherries
Drain pineapple slices and cherries while you prepare the cake batter and pan.

Prepare Pan and Cinnamon Paste
To set up the pan, add a small amount of maple to the cinnamon to create a paste, preventing the cinnamon from lumping. Then, add the rest of the maple to form the mixture.

Make Cinnamon Syrup and Arrange Fruit
Pour the cinnamon syrup into a greased 8 or 9-inch round cake pan. Add pineapple slices and cherries as desired.

Mix Cake Batter
For the cake batter, beat the first three ingredients in a mixer (paddle attachment) or by hand until light, then add the remaining ingredients in segments. Stop mixing as soon as the batter forms to prevent overmixing.

Pour Batter Over Fruit
Use a scoop to gently pour the batter over the fruit and maple base in different spots so it is easier to spread and the syrup doesn’t come up the sides too much. Carefully spread in an even layer.

Bake Until Golden Brown
Bake for 30-40 minutes until golden brown and springy on top.

Cool and Flip onto Platter
Let the cake cool for just 10-15 minutes, then flip it onto a platter while it’s still warm.

Variations and Substitutions
Milk: Use skim milk or unsweetened almond milk to reduce points.
Fruit: Substitute cherries with pears, apples, berries, or bananas.
Sugar: Use sugar instead of a zero-calorie sweetener; note that it raises points from 4 to 9 per slice.
Cake Mix: Use a cake mix for convenience, but be aware it typically has higher points.
Pineapple Cut: Use pineapple tidbits or chunks, drained, or fresh pineapple instead of canned rings.
Serving:Add vanilla glaze, ice cream, whipped cream, or a dessert sauce made from excess pineapple juice. Sprinkle with toasted coconut if desired.

Tips and Tricks for Making Old Fashioned Pineapple Upside Down Cake
1. Flip While Warm: Flip the cake while it’s still warm, about 10-15 minutes after baking, to prevent sticking to the pan.
2. Storage: Store leftovers tightly wrapped in the refrigerator for up to 5 days. Freeze for up to two months, but consume soon as it may separate or get watery over time.
3.Golden Brown and Cracked Top: Bake until golden brown with cracks on top; it should spring back when gently pressed.
4. Drain Pineapple: Don’t skip draining the pineapple to avoid affecting the cake’s texture with excess juice.