Place warm water, milk, shortening, salt, flour, sugar, and yeast into a bread machine in the order listed, or follow the order recommended by the manufacturer if different. Select cycle; press Start.
If your machine has a Fruit setting, add raisins at the signal or about 5 minutes before the kneading cycle has finished.
Remove dough from the machine after the first rising cycle has finished. Turn dough out onto a lightly floured surface and roll out into a rectangle. Spread dough with 2 tablespoons softened butter, then sprinkle with brown sugar and cinnamon. Roll up dough tightly, then cut in half. Place loaves into 2 lightly greased 9x5-inch loaf pans. Cover with a dish towel and let rise in a warm place until doubled in size, about 1 hour.
Preheat the oven to 350 degrees F (175 degrees C).
Brush tops of risen loaves with 1 tablespoon melted butter.
Bake in the preheated oven until crust is brown and loaves sound hollow when tapped, 30 to 40 minutes.