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Step 1
Reserve a handful of strawberries for garnishing the top of the cake. Place the remaining strawberries in a large bowl. Sprinkle granulated sugar over top. Stir to combine and set aside.
Step 2
In a tall bowl, whip the heavy cream with a stand mixer or electric hand mixer on high speed, until you can start to see a trail of the mixer through the cream. Add the vanilla extract and 1/4 cup powdered sugar. Whip until stiff peaks form. (In other words, when you turn off the blender and lift the beaters out of the cream, the cream should stand up on the end of the beater). Set aside.
Step 3
Line a 9 x 5-inch loaf pan with plastic wrap use enough to have excess that you can wrap over the top. Layer 1/3rd of the whipped cream into the pan. Spoon half of the strawberries in an even layer on top of the whipped cream. Top with a layer of graham crackers, breaking them if necessary to fit the pan.
Step 4
Next, add another 1/3rd of the whipped cream, smoothing it out evenly with a spatula. Add the remaining strawberries evenly over the whipped cream. Top with a layer of graham crackers, breaking them if necessary to make them fit. Pull the excess plastic wrap over the top to cover. Freeze for 3-4 hours.
Step 5
Meanwhile, add the remaining 1 3/4 cups powdered sugar and pudding mix to the remaining whipped cream. Whip until it comes together. Refrigerate until ready to use.
Step 6
Remove the cake from freezer, unwrap the top of the cake, and invert the loaf pan onto a plate. Remove the plastic wrap and frost with the whipped cream icing and sprinkle remaining strawberries on top. Freeze until ready to serve. To slice, run your knife under hot water to warm the knife. Dry it off if necessary, then cut the cake. The knife should slide through the cake more easily. Repeat as necessary.
Step 7
Serve and enjoy!