• In a large mixing bowl, beat 4 ounces of softened cream cheese using an electric hand mixer or stand mixer. Beat until it’s light, fluffy, and smooth—about 1 ½ to 2 minutes.
• Pour the dry vanilla pudding mix into the bowl with the cream cheese, along with ¼ cup of the milk. Mix until well combined. The mixture will be thick at this stage—don’t worry, that’s exactly what you want.
• Slowly add in the remaining 1 ¼ cups of milk, mixing as you go. Continue beating until everything is fully incorporated. A few small lumps are perfectly fine!
• Drop in 3 tablespoons of strawberry jam by the spoonful, then use a knife to gently swirl it into the pudding mixture. Don’t overmix—you want visible strawberry streaks running through the filling for flavor and visual appeal.
• Gently fold in half of the thawed Cool Whip using a spatula. Take your time with this step to preserve that light, airy texture. The result is a fluffy, creamy filling with beautiful ribbons of strawberry jam.

Layering Steps

• Spread a very thin layer (about ¼ cup) of the pudding mixture across the bottom of your deep 8-inch or 9-inch square dish. This helps the graham crackers stick and keeps them in place.
• Place a layer of graham crackers over the pudding mixture, breaking pieces as needed to form a complete layer that covers the bottom.
• Spread ⅓ of the remaining pudding mixture evenly over the graham crackers. Top with ⅓ of the sliced strawberries.
• Continue layering in this order: graham crackers, pudding mixture, strawberries—two more times, using up all the filling and fresh berries.
• Finally, spread the remaining half of the Cool Whip over the top of the cake, smoothing it into an even layer.