In a large mixing bowl, beat the softened cream cheese, 1/4 cup granulated sugar, and vanilla extract until smooth and creamy.
In a separate bowl, whip the heavy cream until stiff peaks form.
Gently fold the whipped cream into the cream cheese mixture until fully combined and fluffy.
Combine the diced strawberries with 2 tablespoons granulated sugar. Let them sit for 10 minutes to release their juices.
Mix the crushed shortbread cookies or graham crackers with melted butter until the mixture resembles wet sand.
Lay a crepe flat on a clean surface. Spread a layer of cheesecake filling evenly over the crepe.
Sprinkle a layer of cookie crumbs over the filling.
Add a spoonful of macerated strawberries across the center.
Carefully roll the crepe tightly into a log shape. Repeat with the remaining crepes.
Wrap each roll tightly in plastic wrap and refrigerate for at least 1 hour to allow the Sweet Strawberry Shortcake Cheesecake Rolls to firm up.
Remove from the refrigerator and slice into 1-inch rounds.
Dust generously with powdered sugar before serving.