Mix yeast, warm water and 1 tbsp sugar together in a bowl; let stand for 5 minutes until bubbly. Add milk, butter, 1/2 flour, salt, and remaining sugar; mix with an electric mixer until combined and no longer lumpy. Add rest of flour and knead in by hand for 5 to 6 minutes. Cover and let rise for 1 hour.(Alternatively, use the soft dough cycle on your bread maker.).
Spray a fluted ring pan with cooking spray. Mix the brown sugar and cinnamon together in a bowl. Deflate the dough, pinch off a tablespoon, roll between palms (it helps to lightly oil hands as dough is very sticky), dip ball into melted butter, then roll in brown sugar mixture. Place evenly around the ring pan. Cover with plastic wrap and let rest overnight in refrigerator.
In the morning, remove the pan. Place in preheated oven (350 F). Bake for 30 to 35 minutes. Let sit for 5 minutes before turning onto serving plate. Stir together the confectioner's sugar, milk, and orange extract; pour evenly over bread. Garnish with candied citrus peel (Recipezaar #5319), if desired.