Cook the Tortellini: Bring a large pot of salted water to a rolling boil. Add the cheese-filled tortellini and cook according to package directions, typically for 3-4 minutes, until tender but firm.

Prep the Cheese: While the tortellini is cooling, slice the pepper jack cheese into 18 bite-sized cubes.

Assemble the Skewers: Thread one green olive onto each skewer, followed by a cube of pepper jack cheese, two pepperoni slices, and finally a tortellini.

Serve or Chill: Once assembled, serve immediately or refrigerate in an airtight container. Drizzle with Italian dressing before serving.