In a skillet over medium heat, cook the bacon until it is golden brown and crispy, about 6–8 minutes. Transfer to a plate lined with paper towels, then chop into bite-sized pieces.

Bring a large pot of salted water to a rolling boil. Add the tortellini and cook according to the package instructions until al dente, typically 2–4 minutes. Drain and rinse under cold water.

In a large mixing bowl, combine mayonnaise, red wine vinegar, and a pinch of salt. Add oregano, Italian seasoning, garlic powder, and red pepper flakes. Whisk until smooth and creamy.

Once the tortellini has cooled, add it to the dressing along with pepperoncini, Parmesan cheese, red onion, and cherry tomatoes. Toss together until coated.

Cover tightly with plastic wrap or transfer to an airtight container. Refrigerate for at least 2 hours to allow flavors to meld.