Make the Cheesecake Filling: Beat the cream cheese, sugar, and vanilla until smooth. Whip the heavy cream separately, then fold it into the cream cheese mixture.
Macerate the Strawberries: Toss the diced strawberries with sugar and let them sit for 10 minutes.
Prepare the Cookie Crumb Layer: Mix the crushed cookies with melted butter until crumbly.
Assemble the Rolls: Spread cheesecake filling on each crepe, sprinkle with cookie crumbs, and add a spoonful of strawberries. Roll tightly.
Chill & Serve: Refrigerate for at least 1 hour before slicing. Dust with powdered sugar before serving.