Prepare the Cream Cheese Mixture: In a mixing bowl, beat 8 oz softened cream cheese with 1/4 cup granulated sugar and 1 teaspoon vanilla extract until smooth and creamy.
Whip the Cream: In a separate bowl, whip 1 cup heavy whipping cream until stiff peaks form. Gently fold the whipped cream into the cream cheese mixture to maintain the airy texture.
Macerate the Strawberries: In another bowl, combine 1 cup diced fresh strawberries with 2 tablespoons granulated sugar. Allow the mixture to sit for about 10 minutes so the strawberries can release their juices.
Prepare the Crust: In a mixing bowl, combine 1 1/2 cups crushed shortbread cookies (or graham crackers) with 1/4 cup melted unsalted butter. Mix until the crumbs resemble wet sand, which will aid in the formation of the crust.
Assemble the Rolls: Take one large crepe or thin cake layer and spread a generous layer of the cream cheese filling evenly across the surface. Sprinkle a layer of cookie crumbs and dollop some macerated strawberries on top. Carefully roll the crepe tightly, securing the filling inside.
Chill and Set: Wrap the rolled crepes in plastic wrap, ensuring they are tightly sealed. Refrigerate for at least 1 hour to allow the rolls to set and flavors to meld.
Slice and Serve: After chilling, remove the rolls from the refrigerator, unwrap, and slice into 1-inch pieces. Dust lightly with powdered sugar before serving.