Place water, egg, bread flour, white sugar, powdered milk, salt, 5 tablespoons butter and yeast in bread machine in the order suggested by the manufacturer. Select DOUGH setting, and turn machine on.
Meanwhile; in a small saucepan, melt 1/3 cup butter. Add 1/2 cup brown sugar and ice cream; bring to a boil, and cook for 2 minutes. Pour caramel into the bottom of a lightly greased 9 x 13 inch pan.
Preheat oven to 350 degrees F (175 degrees C).
When machine has finished cycling remove dough from pan and turn it out onto a lightly floured surface. Pat dough into a rectangle. Spread with softened butter and sprinkle lightly with cinnamon. Crumble 1/2 cup brown sugar over the top. Roll up, and seal edge. Cut into 12 rolls, and place in prepared pan of caramel. Allow to rise until doubled in size, about 45 minutes.
Bake at 350 degrees F (175 degrees C) for approximately 20 to 25 minutes, until golden brown.