Preheat oven to 400˚F. Trim the top of the garlic bulb and place in a casserole dish. Drizzle the garlic cloves with olive oil, cover the dish, and roast in a preheated oven for 30-45 minutes until garlic is soft. Remove from the oven and set aside to cool.
When the garlic is cool enough to handle, squeeze the cloves out of the paper shell into a small bowl. Add 2 tablespoons of extra virgin olive oil, mash the roasted garlic with a fork, and stir to combine.
To Make the Dough:
In a large bowl, dissolve the yeast in the warm water. Add the garlic mixture, milk, sugar, salt, and rosemary. Mix to combine ingredients. Add 2 1/2 cups flour a little at a time and mix until the dough comes together. If the dough is sticky, add more flour a tablespoon at a time.
Knead the dough until smooth and elastic, about 5 minutes.
Shape the dough into a ball and place in an oiled bowl. Turn the dough over to oil the top, cover the bowl with a clean kitchen towel, and let the dough rise in a warm place until doubled, about 45-60 minutes.
When the dough is doubled in size, punch it down, and turn onto a lightly floured surface. Shape into a 12-inch long oval loaf. Place the loaf on an oiled baking sheet, cover, and let the dough rise in a warm place until doubled, about 30-45 minutes.
Preheat your oven to 400˚F when your dough is almost finished rising.
Using a sharp knife, lightly cut four slashes diagonally across the loaf. Bake until the bread is golden brown, 20-25 minutes. Remove the bread from the oven and cool on a wire rack. Makes one loaf.