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Step 1
[b]To make freshly whipped cream: [/b]With a hand mixer or in the bowl of a stand mixer, whip 2 cups of heavy cream until it just holds soft peaks. Add 1/3 cup of powdered sugar, 1/2 teaspoon of vanilla extract and whip to combine until stiff peaks hold. Do not overmix. Set aside 1/2 cup whipped cream for topping.
Step 2
In a separate large bowl, make the pudding according to package directions using the 2 cups of cold milk. Allow 5 minutes to thicken. Once thickened, fold in the 3 cups of whipped cream.
Step 3
[b] Assemble the cake: [/b]Spread a thin layer of the cream mixture in a 8 x 8 pan to coat the bottom.
Step 4
Place 3 graham crackers across the center of pan and then break up 1 or 2 more crackers as needed to fill in the gaps. Spread half of the cream mixture on top. Place a single layer of sliced strawberries.
Step 5
Top with another layer of graham crackers, breaking them as needed to make them fit. Spread the remaining cream mixture over top. Add another layer of strawberries.
Step 6
Top with the final layer of graham crackers. Spread the reserved 1/2 cup freshly whipped cream (or Cool Whip) over evenly.
Step 7
Place the last layer of the prettiest berries reserved for the top. Sprinkle on graham cracker crumbs on top.
Step 8
Refrigerate for at least 4 hours or overnight until the graham crackers have softened completely. Serve chilled and dust with powdered sugar if desired.