Marilyn’s Weight Watchers Pineapple Upside Down Cake

Pineapple upside-down cake is a retro favorite that you can now make in a Weight Watchers-friendly version! This delicious recipe uses zero calorie sweetener in the cake mix to make it lower in points than the traditional recipe. However, the cake still retains its soft and tender crumb thanks to canola oil.

For the pineapple base, I use maple syrup instead of brown sugar to reduce the point amount while still giving the pineapple a lovely caramelization. The maple flavor, combined with cinnamon, makes this cake absolutely delicious. To create a classic design, decorate the cake with pineapple slice rings and maraschino cherries, which add a pop of color and sweetness.

Why You Should Try This Recipe

There are plenty of reasons to try this recipe for WW upside down pineapple cake! Here are just a few reasons:

• Simple Ingredients: The only specialty ingredient is the zero-calorie sweetener, and since it is a 1:1 substitute, it functions the same way as granulated sugar. Besides that, all of the ingredients are simple baking staples that you’ve likely worked with many times. It is effortless to throw the ingredients together and get the cake in the oven!
• Timeless Recipe: Everyone loves caramelized pineapple upside down cake! This classic dessert is perfect in both casual and more formal settings. You can make it on a weekday when you have a sweet tooth or for a fancier celebration.
• Low Points: Indulge in your favorite dessert without worrying about exceeding your daily or weekly points. At just four points per slice, you can treat yourself without guilt and stay on track with your weight loss goals.

• Serving Size: 1 slice (99 g)
• Number of Servings: 10
• Time to Cook: 30 – 40 min
• WW Points: 4 per serving

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)

1. Preheat the oven to 350°F.
2. Drain pineapple slices and cherries while you prepare the cake batter and pan.
3. 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.
4. Pour the cinnamon syrup into a greased 8 or 9-inch round cake pan. Add pineapple slices and cherries as desired.

5. 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.

6. 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.

7. Bake for 30-40 minutes until golden brown and springy on top.

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

Variations and Substitutions

Note that these swaps might affect the WW Points but won’t affect how the cake bakes.

• Milk: You can use skim milk or another type of milk if you wish. I used unsweetened almond milk because it has fewer points than skim.
• Fruit: You can skip the cherries and include other fruits with the pineapple, such as pears, apples, berries, or even bananas. Many fruits do well in an upside-down cake, so feel free to get creative!
• Sugar: You can use sugar instead of zero-calorie sweetener here, but it raises the WW points from 4 to 9 points per slice.
• Cake mix: If you wish to take a shortcut, you can use cake mix instead for this recipe! However, I find that the yellow cake mix of popular brands (Pillsbury, Betty Crocker, etc.) is usually 8-9 points a slice. But there are certain zero-sugar mixes that would give you a points amount about the same as this from-scratch cake. However, homemade is always better, so I suggest sticking to the recipe if you have the time.
• Pineapple cut: You don’t have to use the rings; you can also use pineapple tidbits or chunks here, as long as they are drained! You can also use fresh pineapple instead of canned.
• Serving: If you have extra points to use, you can serve this with a simple vanilla glaze, some ice cream, or whipped cream, or you can even use the excess pineapple juice to make a dessert sauce! I also like sprinkling toasted coconut over top of it sometimes.

Tips and Tricks for Making Old Fashioned Pineapple Upside Down Cake

• For this Pineapple upside-down cake recipe, flip the cake while it is still partially warm. You only need to wait 10 – 15 minutes after it comes out of the oven. Otherwise, it might stick to the pan!
• If you have any leftovers, tightly wrap the cake and store it in the refrigerator. It will last approximately 5 days, but it might start to separate or get watery after a few days, so try to consume it as soon as you can. You can also freeze it for two months.
• The cake should look golden brown with some cracks on top before you remove it from the oven. It should also spring back up if you gently press it with your finger. Remember that you are going to flip it, so cracks are okay!
• Don’t skip draining the pineapple. The juice will affect the liquid content in the cake and negatively affect its texture.