Bring a large pot of salted water to a boil. Add 8 ounces of elbow macaroni and cook until al dente, about 8-10 minutes. Drain and rinse under cold water.

Chop 1/2 cup of black olives, slice 3 green onions, and dice 1/2 cup of roasted red peppers.

In a large mixing bowl, combine 1 cup of mayonnaise, 2 tablespoons of red wine vinegar, 2 teaspoons of sugar, 1 tablespoon of milk, and a splash of pickle juice. Season with salt and pepper, and whisk until smooth.

In a large serving bowl, add the cooled macaroni and three-quarters of the dressing. Stir to coat. Fold in the olives, red peppers, pickles, and green onions, tossing gently.

Taste and adjust the seasoning as necessary, adding more dressing and pickle juice if needed.

Cover and refrigerate for at least 2 hours before serving. Stir before serving.