Mise en place. Proof the yeast in water in small bowl.
In stand mixer, mix milk, egg, butter, sugar, 4 cups of flour, pudding, and cake mix until well-mixed. Add yeast and mix until well-mixed and dough pliable. Add extra cup of flour if needed. The dough is going to be a little softer/cakier than regular cinnamon rolls. Don’t “over-flour”!
On a floured surface, roll the dough out into 18” by 30” rectangle. Spread the softened butter over the dough. Mix brown sugar and cinnamon together; then sprinkle over dough, making sure to get up to the edges.
Roll up starting at the long edge. Since the dough is a little “cakier” than normal rolls, might have to use a scraper if dough sticks. Cut into 12 rolls.
Place rolls in greased 9” x 13” baking pan. Cover and let rise in a warm place 1 to 1 & 1/2 hrs. They won't rise as much as normal rolls…they will rise more as they bake.
Bake at 350° for 15-20 min. or until toothpick comes out clean.
For frosting, beat together cream cheese, butter, vanilla, and milk. Add powdered sugar and cinnamon, and whip until smooth. Spread on warm rolls and serve immediately.