Mix warm milk, 1 tbsp sugar, and yeast. Let sit until foamy (5-10 min).
Combine remaining sugar, butter, eggs, vanilla, and food coloring with yeast mixture. Add flour, cocoa, and salt to form dough.
Knead until elastic. Let rise until doubled (60-90 min).
Mix brown sugar, sugar, and cinnamon for filling.
Roll dough into 18×14-inch rectangle. Spread with butter and sprinkle with filling.
Roll tightly from long edge and cut into 12 slices.
Place in greased dish. Rise again (30-45 min).
Bake at 350°F for 20-25 minutes.
Beat cream cheese, butter, powdered sugar, vanilla, and milk for glaze.
Spread glaze over warm rolls.