In a large skillet over medium heat, cook the chopped bacon for 8–10 minutes until crispy and golden brown.

Bring a pot of salted water to a boil. Add cheese tortellini and cook according to package instructions, about 3–5 minutes. Drain and rinse under cold water.

In a 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.

Add the cooked tortellini, chopped pepperoncini, Parmesan cheese, red onion, and halved tomatoes to the bowl. Gently fold to combine.

Cover the salad tightly and refrigerate for at least 2 hours to allow flavors to meld.

Before serving, stir the salad and taste to adjust seasoning. Serve cold or at room temperature.