In a skillet over medium heat, cook the bacon until crispy, about 6–8 minutes. Drain grease and chop.

Bring a large pot of salted water to a boil. Cook tortellini according to package instructions, about 5–7 minutes, then drain and rinse with cold water.

In a mixing bowl, combine mayonnaise, red wine vinegar, salt, oregano, Italian seasoning, garlic powder, and red pepper flakes. Stir until smooth.

Add cooked tortellini, bacon, pepperoncini, Parmesan cheese, red onion, and tomatoes to the bowl. Toss gently to combine.

Cover and refrigerate for at least 1 hour to allow flavors to meld.

Stir before serving and enjoy chilled or at room temperature.