If you love the warm, buttery sweetness of pineapple upside down cake and the creamy richness of cheesecake, then this layered pineapple upside-down cheesecake trifle is going to be your new favorite dessert. It has all the tropical flavor and showstopping presentation you want for a summer party, potluck, or anytime treat. With soft cubes of angel food cake, a velvety cream cheese and pudding filling, sweet caramelized pineapple, and toasty coconut in every bite, it is guaranteed to impress.

Pineapple Upside-Down Cheesecake Trifle

It comes together easily and makes a big batch, which is perfect when you need something a little extra for a gathering. If you are a fan of layered desserts, be sure to check out my Blackstone Breakfast Recipes Roundup for crowd-pleasing ideas or grab some savory inspiration with the Blackstone Dinner Recipes Roundup.

This Pineapple Upside Down Cheesecake Trifle looks fancy in a glass trifle dish, but you do not need anything special to pull it off. You can layer it up in a big mixing bowl or even assemble it in individual mason jars for a fun, portable dessert. Just plan for a little chill time to let all the flavors come together before you dig in.

What You Will Love About This Recipe

It is easy to make ahead which means less stress when entertaining

It feeds a crowd and looks impressive on any dessert table

Every bite is packed with flavor from buttery brown sugar pineapple to fluffy cream cheese filling and toasted coconut

No baking required if you use store bought angel food cake

Fun to customize with fresh pineapple, extra cherries, or mini trifle cups for individual servings

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

Toast your coconut in a dry skillet for a few minutes over medium heat until golden and fragrant
Let the pineapple mixture cool completely before layering to avoid melting the creamy filling
Use a serrated knife to cut the angel food cake into even cubes without squishing it
Fold the pudding mixture into the cool whip slowly to keep the filling light and fluffy
Make it a day ahead to let the flavors soak in and the layers set nicely

FAQs

Yes, this dessert actually tastes better after chilling for a few hours or overnight. Just wait to add the garnish until serving so it stays fresh.

Absolutely. Just be sure to cut it into small tidbits and cook it down with a little sugar and juice to get that rich syrupy flavor.

Vanilla pudding works great as a substitute. You could also use cheesecake flavored pudding for an extra creamy twist.

Sure. If you are not a fan of coconut, you can leave it out or replace it with crushed nuts or graham cracker crumbs for a different texture.

You can, but the texture will be a bit looser. Stabilized whipped cream is a better swap if you want to make it from scratch and keep the layers firm.

Pineapple Upside-Down Cheesecake Trifle

Name: Pineapple Upside-Down Cheesecake Trifle
Prep time: 30 min
Total time: 30 min
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

Prep Time: 30 minutes

Total Time: 30 minutes

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.

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

Melissa

I’m Melissa, the imaginative force behind Sparkles to Sprinkles, where creativity comes to life, and sprinkles of joy are scattered generously. Melissa is a proud Jersey girl who found love with a New York boy. As a mom to four wonderful boys and a few fur babies, her journey into the world of blogging began after making the life-changing decision to stay home and raise her children. Previously a dedicated workaholic, Melissa’s blog became her creative outlet and passion project. Inspired by her mother-in-law, a masterful cook renowned for her delicious home-cooked meals and legendary holiday feasts (think mouthwatering sausage stuffing), Melissa honed her culinary skills through a combination of family recipes and countless cooking classes. She often attended these classes with her son Michael, who shared her enthusiasm for cooking from a young age. Melissa’s love for learning extends beyond familiar cuisines, as she enjoys exploring international recipes in hands-on cooking classes. Her blog features a diverse array of recipes, showcasing her expertise with various kitchen appliances such as the Instant Pot, air fryer, Slow Cooker, Ninja Foodi, Instant Vortex Plus, and more. Join Melissa on her culinary adventures as she shares tried-and-true family favorites alongside exciting new discoveries!

Tropical Pineapple Upside-Down Cheesecake Trifle