• First, take the cream cheese out of the box and let it sit on the counter for 30 to 60 minutes to soften. This will make the cheese mixture easier to spread.
  8 ounces cream cheese
• In a small bowl, mix the softened cream cheese with the dry ranch dressing mix until smooth and creamy with no lumps.
  3 tablespoons dry ranch dressing mix
  

Prep the Pickles and Ham

• Trim both ends off the whole dill pickles.
  16 ounces dill pickles
  
• Pat the pickles completely dry with paper towels. This is the step that keeps the rollups from getting soggy.
• Lay the ham slices flat on a cutting board and pat them dry too.
  ½ pound ham
  

Assemble the Rollups

• Using a butter knife or small offset spatula, spread the cream cheese mixture evenly over each ham slice all the way to the edges.
  
• Place a trimmed pickle at one edge of a ham slice and roll it up tightly around the pickle. Press a toothpick through to hold it if needed.
  

Slice and Chill

• Cut each rolled ham into 3/4 inch pieces and arrange on a serving platter in an even layer.
  
• Cover the tray tightly with plastic wrap and refrigerate for at least 30 minutes before serving. They can be made up to 2 days ahead.