Set out cream cheese to soften to room temperature (I usually leave out a few hours). When you're ready to make, cut each 8 oz block into 8 equal squares.

At least 30 minutes in advance: To absorb excess moisture. Line pickles in a single layer, a couple inches apart on a small stack of paper towels. Place a few more paper towels on top, press gently. Place two slices of ham side by side on another stack of paper towels, place a layer of paper towels on top, followed by two more slices of ham. Repeat process until all ham is layered between paper towels.

Working one at a time place a slice of ham on a cutting board or plate. Using a butter knife or off-set spatula, spread the cream cheese evenly over the slice of ham. Begin at one end working toward the other end, leaving about 1/4 in. cream cheese free to accommodate spreading as you roll.

Place a pickle across the width of the cream cheese covered ham at the end where cream cheese meets the edge. Roll up semi-tightly, careful to not squeeze cream cheese out the edges or rip ham. Repeat process until all 16 are rolled.