Whip the Filling: In a medium bowl, beat the softened cream cheese, powdered sugar, and vanilla extract together using a hand mixer or a sturdy spatula until the mixture is completely smooth, creamy, and free of lumps.
Prep the Wrappers: Unroll the Fruit Roll-Ups onto a clean, flat surface or a sheet of parchment paper. Remove any plastic backing sheets.
Spread: Using an offset spatula or the back of a spoon, spread a thin, even layer of the cream cheese mixture across each fruit sheet, leaving a tiny quarter-inch border around the edges to prevent the filling from squeezing out.
Add Texture: Evenly sprinkle a generous layer of graham cracker crumbs directly over the cream cheese layer. Gently press down on the crumbs with your fingers so they embed slightly into the cream.
Roll Up: Starting from one end, carefully and tightly roll each Fruit Roll-Up into a log shape, just like a mini jelly roll or sushi roll.
Slice: Use a very sharp, smooth-edged knife to slice each log into 3 to 4 bite-sized pieces.
Chill: Arrange the bites on a plate or small baking sheet lined with parchment paper. Refrigerate for at least 30 minutes before serving. Chilling firms up the cream cheese filling, making them much easier to handle and giving them a clean, refreshing bite.