Bring a large pot of salted water to a boil. Add the pasta and cook until al dente according to package directions. Drain and rinse under cold water to cool.
While the pasta cooks, heat a skillet over medium heat and cook the bacon until crisp. Transfer to paper towels to drain, then chop into bite‑size pieces.
In a large bowl whisk together the mayonnaise, sour cream, ranch seasoning mix, apple cider vinegar, and sugar (if using) until smooth and creamy. Season with a few grinds of black pepper.
Add the cooled pasta to the dressing and toss gently to coat evenly.
Fold in the chopped bacon, celery, red bell pepper, green onion, cheddar cheese, and olives if using. Mix until everything is well combined.
Taste and adjust seasoning with more ranch mix or pepper if desired.
Cover and chill in the refrigerator for at least 30 minutes to let flavors meld.