Boil the macaroni in salted water until al dente, 7–9 minutes. Drain and rinse under cool water.
Whisk mayonnaise, sour cream, pickle brine, Dijon, sugar, garlic powder, onion powder, salt, and pepper in a large bowl.
Stir in the chopped pickles, celery, red onion, cheddar, and fresh dill.
Fold in the cooled macaroni until everything is coated and creamy. Taste and adjust seasoning.
Chill 20–30 minutes to let flavors meld. Dust with paprika before serving.