In a skillet over medium heat, cook the chopped bacon until crispy, about 5-7 minutes. Transfer to a paper towel-lined plate to drain and cool.

Bring a large pot of salted water to a boil. Cook the frozen cheese tortellini according to package instructions, about 3-5 minutes. Drain and rinse under cold water to cool.

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

In a large bowl, combine tortellini, crispy bacon, chopped pepperoncini, diced red onion, halved cherry tomatoes, and grated Parmesan. Drizzle with dressing and toss gently.

Cover the bowl and refrigerate for at least 2 hours to let flavors meld.

Before serving, stir the salad to redistribute dressing and garnish with extra Parmesan.