Add vanilla pudding and banana cream pudding mix to a large bowl, then pour in the cold milk. Use an electric mixer to blend until fully combined and thickened (about 2-3 minutes).

In a separate bowl, blend softened cream cheese with vanilla extract, cinnamon, and sweetened condensed milk until smooth and creamy.

Pour cream cheese mixture into pudding mix and gently combine. Fold in one container of cool whip without over mixing.

Begin layering: add pudding mixture to the bottom of your dish, then layer chessman cookies, nilla wafers, bananas, and strawberries. For a clear dish, layer strawberries on the edges for presentation.

Drizzle strawberry glaze over the layers, then add another layer of pudding mixture. Repeat layering until dish is full or ingredients run out.

On the final layer of pudding, spread the cool whip topping evenly. Decorate with leftover strawberries, crushed nilla wafers, and any remaining strawberry glaze.

Lightly cover with plastic wrap and refrigerate for at least 30 minutes (preferably overnight) before serving. Enjoy!