Heat ½ tablespoon olive oil in a large skillet over medium heat. Add the tortellini and water. Cook, stirring occasionally, until the water evaporates and the tortellini becomes tender, about 5–7 minutes.
Add the remaining ½ tablespoon olive oil and continue cooking for 3–5 minutes, stirring occasionally, until the tortellini develops golden, crispy edges. Remove from heat.
While the tortellini cooks, heat a separate skillet over medium heat. Add the prosciutto and cook for 2–3 minutes per side, or until crisp. Transfer to a paper towel-lined plate and let cool slightly before breaking into bite-sized pieces.
In a large serving bowl, combine the chopped arugula and halved cherry tomatoes.
Prepare the dressing by adding the lemon juice, garlic, Dijon mustard, olive oil, Parmesan cheese, salt, and pepper to a blender or food processor. Blend until smooth. Alternatively, finely mince the garlic and shake all dressing ingredients together in a mason jar until well combined.
Add the warm tortellini and crispy prosciutto to the salad. Pour the dressing over the top and gently toss until everything is evenly coated.
Finish with shaved Parmesan and a drizzle of balsamic glaze, if desired. Serve immediately and enjoy.