These mini pineapple upside-down cheesecake trifles are one of my favorite things to serve in the spring and summer! They are filled with layers of cream cheese filling, pineapple, angel food cake, and topped with toasted coconut. This is the perfect dessert to serve for every occasion. it is definitely one of my favorite no-bake desserts.

Pineapple Upside-Down Cheesecake Trifle

If you are looking for an easy dessert that looks absolutely stunning, then look no further than this pineapple upside-down cheesecake trifle. You can’t help but fall in love with the creamy layers of cheesecake filling, the caramelized pineapple, and the light and airy angel food cake all topped with a dollop of cool whip and toasted coconut. This dessert will make you think you are on the beach soaking up the sun!

It is the perfect dessert to serve at baby showers, BBQs, or when you just feel like making something incredibly delicious to enjoy.

For more summer desserts you will want to grab our lemon bar recipe and our lemon blueberry pound cake.

How to Make Pineapple Upside Down Cheesecake Trifles

In a medium mixing bowl, whisk pudding mix with 1 cup of milk for 2 minutes. Chill 5 minutes.

In a separate large bowl, beat cream cheese with powdered sugar and vanilla until smooth, about 1-2 minutes. Add pudding to the cream cheese mixture and beat to combine.

. Using a silicone spatula, gently fold in 1 tub of cool whip and ¾ cup of the toasted coconut, keeping as much air as possible in the mixture. Cover and refrigerate.

In a medium saucepan, melt butter. Add brown sugar and bring to a boil. Add drained pineapple, stirring gently. Mix cornstarch with reserved pineapple juice and add to simmering sugar mixture. Bring back to a boil and cook until the mixture thickens. This mixture will continue to thicken as it cools. Pour into a bowl and let cool for at least 10 minutes. Place in the fridge or freezer to speed up cooling, if needed.

In a clear, deep sided dish; layer cake cubes, pineapple mixture, and cream cheese mixture, repeating layers to the top of the dish. Garnish the top with pineapple, toasted coconut, and maraschino cherries. This dessert can be eaten right away but will benefit from at least an hour of chill time.

Tips Tricks and FAQs

While I prefer making these in individual mason jars you can make it in a large trifle dish. If you opt to make it this way, you will want to cut your pieces of cake into 1-inch squares. It is possible that you will need 1 ½ to two cakes for a large trifle dish.
Add toasted coconut to the top for a nice crunchy texture. If you prefer you can omit the coconut.
Add the leftover cool whip to the top. I love to pipe it onto the top.
You can use fresh pineapple instead of canned if you prefer. If you choose to do this, you will need to use 3 Tablespoons of water to mix with cornstarch to make a slurry to help thicken the sauce.
Get creative with the containers you serve it in! You can use mason jars, short drinking glasses, clear bowls, or even martini glasses.

Storage

You will want to store your leftover pineapple upside-down cheesecake trifle in the fridge, covered. This will last up to 3 days.

Thanks to the boxed pudding mix will help hold the shape of the whipped cream mixture but over time the cake will begin to get soggy and the dessert will start to be liquidy.

Can you make this ahead of time?

Yes, you can make the pineapple mixture and the cream mixture up to 1 day in advance. I do not recommend assembling your whole trifle until right before serving.

Can you toast sweetened coconut in the microwave?

Yes! You can toast sweetened coconut in the microwave. Place it in a microwaveable safe baking dish for 3 minutes. You will want to stir it every 30 seconds.

Pineapple Upside-Down Cheesecake Trifle

Prep Time: 30 minutes

Total Time: 30 minutes

Ingredients

8 oz cream cheese (1 block), softened
½ cup powdered sugar
1 teaspoon vanilla extract
3.3 oz package white chocolate instant pudding
1 cup milk
8oz tub cool whip
1 cup sweetened toasted coconut flakes, divided
2- 20 oz can pineapple tidbits in juice, drained
3 tablespoons reserved pineapple juice
1 cup brown sugar, packed
6 tablespoons butter
2 tablespoons cornstarch
1 angel food cake, cut into ¼” cubes
Maraschino cherries for garnish
Pineapple rings, tidbits, or fresh sliced pineapple for garnish

Instructions

In a medium mixing bowl, whisk pudding mix with 1 cup of milk for 2 minutes. Chill 5 minutes.
In a separate large bowl, beat cream cheese with powdered sugar and vanilla until smooth, about 1-2 minutes. Add pudding to the cream cheese mixture and beat to combine. Using a silicone spatula, gently fold in 1 tub of cool whip and ¾ cup of the toasted coconut, keeping as much air as possible in the mixture. Cover and refrigerate.
In a medium saucepan, melt butter. Add brown sugar and bring to a boil. Add drained pineapple, stirring gently. Mix cornstarch with reserved pineapple juice and add to simmering sugar mixture. Bring back to a boil and cook until the mixture thickens. This mixture will continue to thicken as it cools. Pour into a bowl and let cool for at least 10 minutes. Place in the fridge or freezer to speed up cooling, if needed.
In a clear, deep sided dish; layer cake cubes, pineapple mixture, and cream cheese mixture, repeating layers to the top of the dish. Garnish the top with pineapple, toasted coconut, and maraschino cherries. This dessert can be eaten right away but will benefit from at least an hour of chill time.

Notes

Depending on your size jar, you should have enough to make 8-10 jars

Nutrition Information:

Yield:

Serving Size:

1
Amount Per Serving: Calories: 644Total Fat: 33gSaturated Fat: 23gTrans Fat: 0gUnsaturated Fat: 8gCholesterol: 57mgSodium: 323mgCarbohydrates: 85gFiber: 4gSugar: 69gProtein: 6g