Beat the softened cream cheese in a bowl until completely smooth with no lumps - about 1 minute with a spatula. This is crucial; cold cream cheese will tear the tortillas.

Fold in the diced pickles, pickle brine, dried dill, garlic powder, and black pepper. The brine loosens the mixture and adds that sharp pickle punch. Mix until evenly distributed.

Lay a tortilla on your counter. Spread about 3 tablespoons of the cream cheese mixture evenly to the edges - too thick and they won't roll tight. If using ham, lay 1 ounce of slices over the cream cheese, pressing gently to adhere.

Roll the tortilla up snugly from the bottom, keeping tension as you go. A loose roll means ugly pinwheels. Wrap each roll tightly in plastic wrap.

Refrigerate the wrapped rolls for at least 1 hour, preferably 2. This firms up the cream cheese so you get clean slices instead of smushed spirals.

Unwrap and slice each roll into 6 even pieces with a sharp knife - wipe the blade clean between cuts for neat edges. Arrange on a platter and sprinkle with fresh dill.