In a mixing bowl, combine softened cream cheese with ranch seasoning. Stir until smooth and well blended. I always make sure there are no lumps so it spreads easily later.
Lay out each slice of ham flat on a clean surface. Spread a generous layer of the cream cheese mixture evenly across each slice. Don’t go too thick, or it might squeeze out when rolling.
Place a whole pickle at one end of each ham slice. Make sure it’s dry by patting it with a paper towel. This helps the roll ups stay firm and not slippery.
Carefully roll the ham slice tightly around the pickle. Keep it snug so the filling doesn’t fall apart. I like to press gently as I roll for a clean finish.
Using a sharp knife, cut each roll into 1-inch pieces. Wipe the knife between cuts for neat slices. Arrange them on a plate, and they’re ready to serve!