Servings & Timing
Prep Time: 10 minutes
Bake Time: 40 minutes
Total Time: 50 minutes
Yield: 12 servings
Dietary Tags: Crowd-Friendly, Kid-Friendly
📝 Ingredients
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Yellow cake mix
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Pineapple slices (canned, drained)
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Unsalted butter, melted
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Brown sugar
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Crushed pineapple (with juice)
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Instant vanilla pudding mix
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Cold milk
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Whipped topping (like Cool Whip)
🔪 Instructions
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Prep the pan
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Preheat oven to 350°F (175°C).
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Pour melted butter into a greased 9×13″ baking dish.
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Sprinkle brown sugar evenly over the butter and arrange pineapple slices on top.
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Make the batter
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Prepare the yellow cake mix according to package directions, replacing the water with crushed pineapple and its juice.
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Pour the batter over the pineapple slices in the pan.
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Bake the cake
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Bake for 35–40 minutes or until golden and a toothpick inserted in the center comes out clean.
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Let the cake cool completely.
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Mix the creamy filling
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In a bowl, whisk together the pudding mix and cold milk until thickened.
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Fold in the whipped topping.
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Assemble
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Slice the cake horizontally and spread the creamy filling between the layers or simply frost the top.
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Chill & serve
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Refrigerate for at least 1 hour before serving for best flavor and texture.
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💡 Notes & Tips
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Want extra pineapple flavor? Brush some pineapple juice on the cake layers before adding the cream.
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Make ahead: Cake and filling can be made a day in advance and assembled before serving.
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No pudding? Vanilla yogurt can be a quick swap in the filling.
📸 Step-by-Step Guide
(Blog photo suggestions: butter/sugar layer → pineapple slices → batter poured over → baked cake → pudding whipped → assembly)
Tip: For cleaner slices, chill the cake fully before cutting.
🥄 Ingredient Insights & Swaps
Ingredient Notes:
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Cake mix: Yellow cake holds up well to the juicy pineapple.
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Butter & brown sugar: Creates a caramelized base.
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Crushed pineapple: Adds moisture and natural sweetness.
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Instant pudding & whipped topping: Keeps the filling light and airy.
Swaps & Variations:
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Lower-fat version: Use light whipped topping and sugar-free pudding mix.
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Fruit swap: Try peaches or mandarin oranges instead of pineapple for a fun twist.
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Dietary note: Gluten-free cake mix works well here if needed.
🎨 Flavor Variations & Serving Ideas
Flavor Ideas:
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Add a sprinkle of toasted coconut for a tropical flair.
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Mix a little rum or coconut extract into the pudding for a pina colada vibe.
Serving Suggestions:
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Serve chilled with fresh berries on the side.
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Pair with iced tea or a light sparkling wine.
🧊 Storage & Make-Ahead
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Storage: Keep covered in the refrigerator for up to 3 days.
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Freezing: Not recommended once assembled (the creamy filling doesn’t freeze well).
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Make-Ahead Tip: Bake the cake up to 2 days ahead and assemble when ready to serve.
🔎 Nutrition & W-W Points (per serving estimate)
Calories: ~280 kcal | Carbs: 35g | Protein: 3g | Fat: 13g
W-W Points (per slice, based on 12 servings):
➡️ 9 Points (standard ingredients: regular cake mix, pudding, whole milk, regular Cool Whip, butter)
➡️ 6 Points if you use sugar-free pudding, light whipped topping, light butter, and 1% milk.
Note: For exact W-W points, input your ingredient brands into the W-W app to confirm based on your plan.
Allergens: Milk, Egg, Wheat (check cake mix for specific allergens)
❓ Frequently Asked Questions
Q: Can I make this as cupcakes?
A: Yes! Layer a small pineapple slice at the bottom of each cupcake liner and bake according to cupcake instructions.
Q: What if I can’t find crushed pineapple?
A: Dice pineapple rings or chunks finely and include some juice.
Q: Can I skip the creamy filling?
A: Absolutely—the cake is moist enough to enjoy without it if preferred.
📝 The Story Behind the Recipe
This recipe is a family reunion classic that has made appearances at nearly every summer gathering. It combines the nostalgic taste of pineapple upside-down cake with a creamy surprise layer that guests love—plus, it’s easy enough to throw together even on busy days.