Prep the raisins: If your raisins are dry, soak them in warm water for 10 minutes, then drain and pat dry. This helps keep the bread extra soft and studded with plump fruit.
Mix the dry ingredients: In a large bowl, whisk together flour, sugar, yeast, salt, and cinnamon until evenly combined.
Add the wet ingredients: Stir in the warm milk, melted butter, egg, and vanilla.
Mix with a spoon until a shaggy dough forms and most of the flour is absorbed.
Knead the dough: Turn out onto a lightly floured surface and knead for 7–9 minutes until smooth and elastic. If the dough sticks, dust lightly with flour, but avoid adding too much.
Fold in the raisins: Gently flatten the dough, sprinkle the raisins evenly, and fold or roll the dough to distribute. Knead lightly just until the raisins are tucked in.
First rise: Place the dough in a lightly greased bowl, cover with a clean towel or plastic wrap, and let rise in a warm spot until doubled, about 60–90 minutes.
Shape the loaf: Punch down the dough to release air.
Pat into a rectangle about 8x12 inches. Roll up tightly from the short side, pinch the seam, and tuck the ends under.
Pan and second rise: Grease a 9x5-inch loaf pan. Place the dough seam-side down in the pan.
Cover and let rise until the top domes 1 inch above the rim, about 35–50 minutes.
Preheat and bake: Preheat the oven to 350°F (175°C). Brush the top with milk or melted butter if you like a softer, shinier crust. Bake 30–35 minutes, until golden brown and the internal temperature reaches about 190°F (88°C).
Cool before slicing: Let the loaf cool in the pan for 10 minutes, then transfer to a wire rack.
Cool at least 45 minutes before slicing to keep the crumb soft and even.