Add ingredients to pan of bread maker machine in the order given.
Set bread maker to "Dough" setting and hit START.
Make the Cinnamon Rolls:
When bread machine signals the end of the dough cycle, press STOP. Remove dough from bread pan.
Grease a 9" x 9" x 2" square pan; set aside.
Roll dough on a lightly floured bread board into a 15" x 9" rectangle. Spread the 2 Tbsp. softened butter evenly over the dough.
Combine 1/4 cup sugar and 2 tsps. cinnamon in a small bowl. Sprinkle this mixture evenly over the buttered dough.
Working from one of the long edges, roll dough tightly. Pinch seam and roll dough so you have a log 15" long, seam side down. It's okay to manipulate the log to make it shorter and consistent in circumference. The dough will be very easy to work with.
Cut the dough log into 9 equal slices, about 1-1/2 inches wide. A small serrated knife works well for this. Place the rolls evenly in the greased baking pan. Cover and let rise about 40 minutes or until the rolls have doubled in size.
Preheat Oven to 375°
Bake cinnamon rolls in preheated oven for 25 to 30 minutes, just until lightly golden brown. Remove pan from oven and place on a wire cooling rack for 10 minutes.
Prepare the Glaze:
Combine powdered sugar, butter, milk and vanilla in a small bowl. Stir until smooth and creamy. Add a drop or two of milk to reach the desired consistency.