Cook the chopped bacon in a large skillet over medium heat until crispy, about 8-10 minutes. Drain excess fat, leaving drippings for flavor.

Bring a pot of salted water to a boil; add frozen cheese tortellini and cook according to package directions until al dente, usually about 3-5 minutes. Drain and rinse under cold water.

In a mixing bowl, whisk together mayonnaise, red wine vinegar, salt, oregano, Italian seasoning, garlic powder, and red pepper flakes until smooth.

Add cooled tortellini, chopped bacon, diced pepperoncini, grated Parmesan, finely chopped red onion, and diced tomatoes to the dressing. Toss gently.

Cover tightly and refrigerate for at least 1 hour to allow flavors to meld.

Before serving, stir the salad, adjust dressing as needed, and serve chilled.