1.In a large bowl, toss flour, 1/4 cup sugar, salt, and yeast together. Set aside. Heat the milk and 3 tablespoons butter together in the microwave until the butter is melted and the mixture is warm to touch (about 110°F). Stir in the 2 tablespoons of orange juice, 1 tablespoon orange zest, and the egg.
2.Combine the butter mixture and the flour mixture and stir until it forms a soft dough. Poke it with your finger, it should bounce back. If not, stir in more flour 1 tablespoon at a time.
3.On a lightly floured surface, knead the dough for 1 minute. Place in a lightly greased bowl and let rest for about 10 minutes. Mix together the cinnamon, 1/4 cup sugar, and 1 tablespoon orange zest. Set aside.
4.Roll the dough out in a 14×8-inch rectangle. Spread 3 tablespoons softened butter on top. Sprinkle the sugar and cinnamon all over the dough. Cut into 10 even rolls and arrange in a lightly greased 9-inch round cake pan.
5.Loosely cover the rolls with plastic wrap and allow to rise in a warm, draft-free environment for 60-90 minutes. After the rolls have doubled in size, preheat the oven to 375°F.
6.Bake for 25-28 minutes until lightly browned. Cover the rolls with aluminum foil after 15 minutes to avoid over-browning on top. Whisk the powdered sugar and 1 tablespoon orange juice together until smooth. Drizzle or spread over warm rolls.