Dissolve 1 tablespoon sugar and the yeast in warm water in a large bowl; let stand for 5 minutes. Lightly spoon flour into dry measuring cups, and level with a knife. Add 1 tablespoon sugar, 1 1/2 cups flour, milk, butter, and salt to yeast mixture; beat with a mixer at medium speed until smooth. Turn the dough out onto a floured surface. Knead the dough until smooth and elastic (about 10 minutes); add enough of remaining flour, 1 tablespoon at a time, to prevent dough from sticking to hands.
Place dough in a large bowl coated with cooking spray, turning to coat top. Cover and let rise in a warm place (85°), free from drafts, 1 hour or until doubled in size. (Press two fingers into the dough. If indentation remains, the dough has risen enough.)
Combine the ham, cheese, olives, and pepper. Set aside.
Uncover dough. Punch dough down; let rest 5 minutes. Roll into a 12 x 8-inch rectangle on a lightly floured surface. Brush mustard over dough, leaving a 1/2-inch margin around edges. Spread ham mixture evenly over dough. Beginning with a long side, roll up jelly-roll fashion; pinch seam to seal (do not seal ends of roll). Place, seam side down, in an 8-inch loaf pan coated with cooking spray. Cover and let rise 30 minutes.
Preheat oven to 375°.
Uncover dough. Combine egg white and 1 tablespoon water; brush over loaf. Sprinkle with Italian seasoning. Bake at 375° for 30 minutes. Loosely cover with foil. Bake for an additional 10 minutes or until loaf sounds hollow when tapped. Remove from pan; cool on a wire rack.