Dice half of the baked loaf into small ½ inch cubes and set aside. (Save the other half of the loaf for eating!)
In a mixing bowl, whisk together the melted butter, sugar, eggs and drained pineapple. Add the bread cubes and fold gently until all of the bread is coated in the mixture.
Spoon into a greased 8-inch square pan. Cover with foil and bake at 350 degrees for approximately 25 minutes (or just until set.) Allow to cool slightly.
Take a spoonful of the pineapple dressing and roll it up in a slice of deli ham. Repeat with the other slices of ham. Place the rolls in a greased 9x13 inch baking dish. Pour the reserved pineapple juice over the ham roll-ups and cover with foil. Bake at 350 degrees for 25-30 minutes or until heated through.
When serving, spoon some of the hot pineapple juice from the bottom of the pan over the rolls.