To prepare the dough, place the yeast, 1/2 tsp sugar, and the warm water in a small bowl. Loosely cover the bowl with a warm, damp towel. Let it sit for 15 minutes.
Pour the milk, butter, salt, and 1 Tbsp of sugar into a small pot set over low heat. Warm up the mixture until the butter melts and the sugar dissolves. Do not boil. Remove the pan from the heat.
Place the flour into the bowl of a stand mixer fitted with the hook (bread paddle) attachment. Add the yeast and milk mixture to the bowl and mix on medium speed until incorporated. Increase the speed to medium-high and mix until the dough forms a ball and pulls away from the sides of the bowl, about 6–8 minutes. Remove the dough and place it in a mixing bowl that has been lightly sprayed with oil. Loosely cover with a warm, damp towel and place the bowl in a warm, humid area in your kitchen. Let the bread rise for 3 hours.
To prepare the loaf, line a baking sheet with parchment paper and spray the paper with cooking spray; set aside.
Place the dough on a lightly floured surface and punch it down. Then, roll it into a 20''L x 16''W rectangle. Line the dough with the ham slices, slightly overlapping each piece and covering the entire surface of the dough, except for a 3/4'' border around the edges. Sprinkle the raisins and olives on top of the ham, scattering them evenly throughout. Fold the 3/4'' border, only from the width sides, in to prevent the filling from leaking out. Lightly brush egg wash along the borders and then roll the bread lengthwise to form a log. (Do not discard the egg wash.)
Place the rolled bread, seam side down, onto the prepared sheet pan. Put a warm damp towel, loosely on top of the bread, place it in a warm and humid area in your kitchen and let it sit for 45 minutes.
Position an oven rack in the bottom-middle part of the oven and preheat to 350°F. Remove the towel from the bread. Carefully dock the bread on the top and sides with a fork. Brush the bread with egg wash, completely covering top and sides. Bake for 45 to 50 minutes, or until golden brown. Let the loaf cool completely before serving.
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