In a small bowl, combine warm milk, yeast, and 1 tablespoon of the sugar. Let sit for 5-10 minutes until foamy. In a large bowl, whisk together the remaining sugar, salt, eggs, and softened butter. Add the yeast mixture and stir to combine.
Add 3 cups of flour and stir until a soft dough forms. Turn out onto a floured surface and knead for 8-10 minutes, adding the remaining 1/2 cup flour as needed until the dough is smooth and elastic. Knead in the raisins until evenly distributed. Place in a greased bowl, cover, and let rise in a warm place until doubled, about 1 hour.
Punch down the dough and turn out onto a lightly floured surface. Roll into a rectangle about 9x18 inches. Brush the surface with melted butter, leaving a 1-inch border. In a small bowl, mix the 1/2 cup sugar and cinnamon. Sprinkle evenly over the buttered dough.
Starting from the short side, roll the dough up tightly into a log. Pinch the seam to seal. Place seam-side down in a greased 9x5-inch loaf pan. Cover and let rise until doubled, about 45 minutes.
Preheat oven to 350°F. Bake the loaf for 35-40 minutes, until golden brown and hollow-sounding when tapped. If the top browns too quickly, tent with foil. Let cool in the pan for 10 minutes, then transfer to a wire rack to cool completely before slicing.