Pineapple Upside Down Ice Box Cake

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7Made this recipe

Serves: 6-8

Prep Time: 20-25 minutes

Cook Time: 2 hours

About Pineapple Upside Down Ice Box Cake

Welcome to a delightful journey of flavors with our Pineapple Upside-Down Ice Box Cake recipe. This dessert combines the nostalgic charm of a classic pineapple upside-down cake with the creamy indulgence of an icebox cake. Layers of tender cake, caramelized pineapple, and a luscious cream filling come together to create a treat that will transport your taste buds to dessert paradise. Whether you’re looking to impress guests at a special gathering or simply satisfy your sweet tooth, this recipe promises a refreshing twist on a beloved classic.



Ingredients for Cake

4 sleeves of graham crackers (about 25 squares)

Ingredients for Pineapple Pudding:

2 cans (20 ounce) pineapple chunks, well drained, (reserve juice)

1-1/2 cups sour cream

3 boxes instant vanilla pudding (3.4 oz. each)

1 cup milk

16 ounces whipped topping

Ingredients for Pineapple Topping:

2 cups chopped pineapple

1 tbsp flour

2 tbsp brown sugar

1/2 teaspoon cinnamon

1/4 cup butter melted

15-20 Maraschino Cherries

Ingredients for Brown Sugar Whipped Cream:

3/4 cup heavy cream

1/4 cup light brown sugar

1/8 teaspoon kosher salt

1 vanilla bean, split and seeds scraped


01To make the pineapple pudding, drain the pineapple chunks well, reserving the juice. Save pineapple chunks for topping.
02Mix the juice with the 3 boxes of vanilla pudding. Add milk and stir until well combined. Fold in sour cream and whipped topping until well combined.
03For the whipped topping, in the bowl of a stand mixer fitted with a whisk attachment, or an electric hand mixer, combine cream, brown sugar, salt, and vanilla seeds. Whip on medium-high speed until fluffy and thick, about 5 minutes. Use immediately or refrigerate for up to 1 week in an airtight container.
04To make the topping, whisk together flour, brown sugar, and cinnamon in a separate medium sized bowl. Then add 2 cups of the drained pineapple chunks from the can. Mix gently to incorporate.
05In 9x13 baking dish smear ¼ cup of the pineapple pudding, until the bottom is covered evenly.
06Then place one layer of graham crackers down, breaking them as necessary to create tight, even layer.
07Layer half of the whipped cream over the graham crackers, again spreading evenly.
08Spread about 1/4 cup of the pineapple mixture over the whipped cream. Then layer once more with graham crackers.
09Spread the remaining pineapple pudding on top of the graham crackers, evenly, smoothing over with the back of a spoon.
10Add another layer of graham crackers. Then spread remaining whipped cream over top, smoothing with the back of a spoon. Add the remaining pineapple mixture over top, drizzle the melted butter over top. Place the maraschino cherries over top as well.
11Cover with plastic wrap and place in the refrigerator for at least two hours, or overnight.

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Heat a tablespoon of butter and a tablespoon of olive oil in a large pan. Wait until the pan is hot and the butter has fully melted.