In a large mixing bowl, whisk together the instant vanilla pudding mix and cold milk until thickened, about 2 minutes. Once thickened, fold in the whipped topping and powdered sugar, mixing until smooth. Stir in the vanilla extract.
Layer the Graham Crackers and Pudding:
In a 9×13-inch baking dish, layer the graham crackers to cover the bottom of the dish. Spread half of the pudding mixture over the crackers, smoothing it out with a spatula. Add another layer of graham crackers, followed by the remaining pudding mixture. Top with a final layer of graham crackers.
Make the Chocolate Topping:
In a small saucepan, melt the chocolate chips and butter over low heat, stirring until smooth. Stir in the milk and vanilla extract until fully combined.
Top the Cake:
Pour the chocolate topping over the final layer of graham crackers, spreading it out evenly with a spatula.
Chill and Serve:
Refrigerate the cake for at least 4 hours, or overnight, to allow the layers to set and the flavors to meld together. Slice and serve chilled.
Serving and Storage Tips:
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