Step 1: Prepare the Cream Cheese Base

In a large mixing bowl, beat the softened cream cheese until smooth and fluffy. Add powdered sugar and continue beating until creamy. This creates the rich, cheesecake-like foundation that makes this pudding special.

Step 2: Mix the Pudding Layer

Add the sweetened condensed milk and blend until fully incorporated. Slowly pour in the cold milk, followed by the vanilla pudding mix. Beat for 2–3 minutes until thickened. Add vanilla extract.

The mixture should look silky, slightly thick, and lump-free.

Step 3: Fold in the Cool Whip

Gently fold in the Cool Whip using a spatula. Don’t overmix—you want a light, airy texture. This creates the velvety, cloud-like pudding layer.

Step 4: Slice the Fruit

Slice the bananas and strawberries just before assembling to keep them fresh. Pat the strawberries gently with a paper towel to remove excess moisture so the pudding layers stay creamy and not watery.

Step 5: Assemble the Layers

Use a trifle dish, 9×13 baking pan, or deep glass bowl.

1. Layer 1: Cookies

2. Layer 2: Sliced bananas

3. Layer 3: Sliced strawberries

4. Layer 4: Cheesecake pudding mixture

Repeat these layers until ingredients are used, finishing with pudding on top.

Step 6: Add the Final Touches

Top with extra strawberries, crushed cookies, or a drizzle of strawberry sauce for presentation.

Cover and refrigerate at least 4 hours, preferably overnight for best flavor.