Cook the bacon in a skillet until crisp. Drain away the rendered grease, then transfer the bacon to a paper towel-lined plate to remove excess oil.
Chop or crumble the cooked bacon into small pieces, then reserve it for assembling the salad.
Bring a pot of water to a boil and prepare the frozen cheese tortellini according to the package instructions, cooking only until al dente.
Drain the tortellini, then rinse it under cold water to halt the cooking process. Set it aside while the remaining components are prepared.
In a large mixing bowl, combine the mayonnaise, red wine vinegar, salt, oregano, Italian herbs, garlic powder, and crushed red pepper flakes.
Stir the dressing thoroughly until the mixture is smooth, evenly seasoned, and fully blended.
Add the cooled cheese tortellini, pepperoncini, grated Parmesan, chopped red onion, halved grape tomatoes, and crumbled bacon to the bowl with the dressing.
Fold the ingredients together gently until the tortellini and salad additions are evenly coated in the creamy dressing.
Cover the bowl and refrigerate the salad for at least 1 hour so the flavors can blend and the salad can become properly chilled.
Before serving, stir the salad well to redistribute the dressing, then transfer it to a serving dish and serve cold.