Heat the oven to 350 °F and line a large baking sheet with parchment paper. Keep the lined pan ready before cooking the filling so the cheese rounds can go straight into the oven.

Cook the ground beef, onion, and bell pepper in a skillet over medium-high heat, breaking up the beef as it cooks, until the meat is fully browned and the vegetables are soft. Drain away excess grease once the skillet stops giving off vigorous moisture and the vegetables look tender.

Stir Worcestershire sauce, cream cheese, and salt and pepper to taste into the beef mixture. Continue stirring until the cream cheese has fully melted and the filling looks creamy rather than crumbly.

Arrange the shredded Monterey Jack into 8 even circles on the prepared baking sheet, then bake for 8 to 10 minutes. Remove the pan when the cheese is bubbling, the edges are lightly browned, and each circle has a delicate lace-like perimeter.

Let the cheese rounds stand for 1 to 2 minutes, spoon filling across the center of each one, and roll them gently into wraps. The cheese should bend without splitting; let the finished rolls cool until the shells firm up before serving.