01 -
In a large bowl, combine vanilla pudding and banana cream pudding mixes with cold milk. Use an electric mixer to blend until fully combined and thickened, about 2-3 minutes.
02 -
In a separate bowl, blend softened cream cheese with vanilla extract, cinnamon, and sweetened condensed milk on high speed until smooth and creamy with no lumps.
03 -
Pour the cream cheese mixture into the prepared pudding and gently combine with a spatula. Fold in one container of Cool Whip carefully to maintain fluffiness.
04 -
Spread a small amount of pudding mixture on the bottom of your trifle dish or serving bowl. Add a layer of Chessman cookies, followed by Nilla wafers, banana slices, and strawberry slices. For visual appeal in a clear dish, place some strawberries against the edge.
05 -
Drizzle strawberry glaze over the layers. Add another layer of pudding mixture and continue alternating layers of cookies, fruits, glaze, and pudding until you reach the top of the dish or exhaust your ingredients.
06 -
Spread the second container of Cool Whip evenly over the final pudding layer. Decorate with remaining strawberries, crushed Nilla wafers, and strawberry glaze.
07 -
Cover lightly with plastic wrap and refrigerate for at least 30 minutes, preferably overnight, before serving.