First, make the cinnamon roll dough. Warm the milk until it reaches about 105F. In a large bowl, add 1 tbsp of sugar and 1 tbsp of yeast to the warm milk. Stir to mix evenly and allow to sit for about 5 minutes until the mixture becomes foamy.
Once the mixture has become foamy, add the 1/3 cup of sugar, butter, eggs, and vanilla. Use a wooden spoon, a hand mixer with dough hooks, or beaters in a pinch to stir until combined. Once combined, add about 4 1/2 cups of flour, salt, and cinnamon. Stir using the dough hooks, starting on low, then slowly increase to high. Once a large ball has formed, transfer the dough to a floured surface, kneading with your hands for about 5 minutes, until the dough becomes smooth and elastic. Form into a ball again, place in a large greased bowl and cover with a warm damp towel. Place the bowl in a warm place to rise for an hour.
In the meantime, make the filling. In a small bowl, combine the butter, brown sugar and cinnamon together until thoroughly combined. Set aside.
Once the dough as doubled in size it is time to assemble the cinnamon rolls. Sprinkle a large work surface with flour. Take the dough out of the bowl, gently pressing the gas out and forming it into a rectangle. With a rolling pin, roll the dough out into at 24x12 inch rectangle, then spread the filling all over the dough. Roll the dough lengthwise to form a tightly formed log, then cut into 12 equally sized rolls. Place the rolls in a greased baking dish, cover and let rise until doubled in size.
While the rolls rise, preheat the oven to 350F and begin making your cream cheese icing. In a medium bowl, mix together the cream cheese, butter, powdered, sugar, vanilla extract, and salt on medium speed with a hand mixer and set aside.
Once the rolls have fully proved, place in the oven at 350F and bake for 18-20 minutes. Once baked, spread with the cream cheese icing. Allow to cool for a few minutes and then serve warm. Enjoy!