In a skillet over medium heat, add diced bacon and cook for about 6-8 minutes until it turns crispy and golden brown. Transfer to a paper towel-lined plate and chop into bite-sized pieces.

Bring a large pot of salted water to a rolling boil. Add the frozen cheese tortellini and cook for about 3-5 minutes until al dente. Drain and rinse under cold water.

In a large mixing bowl, combine mayonnaise, red wine vinegar, oregano, Italian seasoning, garlic powder, and red pepper flakes. Whisk until thoroughly blended and creamy.

Add the cooled tortellini, crispy bacon, pepperoncini, Parmesan, red onion, and tomatoes to the bowl with the dressing. Toss gently until evenly coated.

Cover the bowl with plastic wrap and refrigerate for at least 2 hours to allow flavors to meld. Stir gently before serving.