In a skillet over medium heat, cook the bacon strips until crispy, about 8-10 minutes. Transfer to a paper towel-lined plate and chop.

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

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

Add cooled tortellini, chopped bacon, sliced pepperoncini, red onion, cherry tomatoes, and grated Parmesan to the dressing. Gently fold to combine.

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

Before serving, stir gently and serve in a large bowl or individual servings.