In a large skillet over medium heat, cook the sliced bacon until crispy, about 6 to 8 minutes. Transfer to a paper towel-lined plate to drain, then chop into pieces.

Bring a large pot of salted water to a boil. Add the frozen cheese tortellini and cook according to package instructions, 3 to 5 minutes, until al dente. Drain and rinse under cold water.

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

In a large mixing bowl, combine cooled tortellini, chopped bacon, sliced pepperoncini, red onion, and diced tomatoes. Add grated Parmesan and drizzle with creamy dressing. Fold to combine.

Cover the bowl with plastic wrap and refrigerate for at least 2 hours to meld flavors.

Before serving, stir the salad and add more dressing if needed. Serve chilled or at room temperature.