Warm milk in the microwave for 45-60 seconds. It should be warm but not hot to the touch (about 105 degrees F).
Place milk into the bowl of your standing mixer, add 1 TBS sugar and 1 TBS yeast to the warm milk. Stir and let it sit (proof) for five minutes or until it becomes foamy.
Add the ½ cup sugar, butter, eggs, and vanilla to the mixture in the bowl of your standing mixer. Use a dough hook to stir until combined.
Add 4 cups flour, salt, and cinnamon and stir the dough hook, starting on low and increasing to high.
Knead dough in the standing mixer until a large ball is formed. The dough should be smooth and only slightly tacky to the touch. If too sticky, add more flour 1 TBS at a time until a smooth ball is formed.
Transfer dough to a floured surface and knead with your hands until smooth and elastic (about 3-5 minutes). Form into a ball.
Grease a large bowl, place the dough inside.
Cover the bowl with a warm, damp towel and put in a warm place to rise.
Let the dough rise about 1 hour or until doubled in size.
While dough is rising, make the filling. Combine butter, brown sugar, and cinnamon until mixture is homogeneous. Set aside. Or, combine cinnamon and sugar, then brush dough with melted butter and sprinkle with cinnamon sugar. Alternately, you can combine the cinnamon and sugar. Then melt the butter and brush it on the rolled dough, then sprinkle the cinnamon sugar on the butter-brushed dough. (I think this way is easier)!
Sprinkle a large work surface with flour.
Gently press the gas out of the dough and form into a rectangle.
Roll the dough into a 24x12” rectangle, about ¼ inch thick.
Spread the filling all over the dough.
Roll up dough, cut into 12 equal sized rolls.
Line a 9x13 inch glass baking dish with parchment paper and lightly grease. Place rolls in 4 rows of three, evenly spaced.
Cover and let rise until nearly doubled, about 30 minutes. Preheat the oven to 350 degrees F.
Bake in preheated oven until golden brown, about 18-20 minutes.
While rolls are baking, beat together cream cheese, butter, powdered sugar, vanilla extract, and salt. Keep at room temperature.
Once rolls are removed from the oven, spread the cream cheese frosting on them while they are still warm.
Let cool and serve warm.
To make ahead: Assemble rolls, refrigerate, then bake as per instructions.
To freeze: Assemble rolls, freeze, then thaw, rise, and bake as per instructions.
If filling "oozes out," invert the rolls immediately after baking to reincorporate the filling.