Bring a large pot of salted water to a rolling boil. Add ½ pound of dry pasta and cook until just al dente, about 6-8 minutes. Drain and rinse under cold water.

In a medium mixing bowl, combine ½ cup mayonnaise, 1 tablespoon pickle juice, and 2 tablespoons milk. Whisk until smooth, then mix in salt, pepper, garlic powder, onion powder, dry dill, and cayenne pepper. Chill the dressing.

Dice ¾ cup of dill pickles and cube ¾ cup of cheddar cheese. Drain a 2.5 oz can of sliced black olives.

In a large bowl, combine the cooled pasta, diced pickles, cubed cheese, and drained olives. Pour the chilled dressing over and stir gently to coat.

Adjust seasoning if needed. Serve immediately or chill in the refrigerator for up to 24 hours before serving.