Bring a large pot of salted water to a rolling boil. Add the elbow macaroni and cook for about 7-8 minutes until nearly al dente. Drain and rinse under cold water.

In a medium bowl, whisk together mayonnaise, pickle juice, and milk. Stir in salt, pepper, garlic powder, onion powder, dry dill, and cayenne pepper. Refrigerate for 10 minutes.

Dice the dill pickles and cube the cheddar cheese. Drain the sliced black olives.

In a large mixing bowl, combine the cooled pasta, chopped pickles, cubed cheese, and drained olives. Pour in the chilled dressing and mix until well combined.

Taste and adjust the seasoning if needed. Serve immediately or refrigerate for an hour to enhance flavors.