The Night Before
- Activate the yeast: Warm the milk until it feels warm to the touch, about 105 to 110°F. Pour it into a large bowl or stand mixer bowl, stir in the yeast and 1 tablespoon of the sugar, and let it sit 5 to 10 minutes, until foamy.
- Make the dough: Add the remaining sugar, butter, eggs, and salt, and mix to combine. Add 4 cups (480 g) of the flour and mix until a shaggy dough forms.
- Knead: Knead with the dough hook on medium-low for 6 to 8 minutes, or by hand for about 10 minutes. Add the remaining 1/2 cup of flour a tablespoon at a time, only as needed, until the dough is smooth, elastic, and slightly tacky but doesn’t stick to a clean finger.
- First rise: Place the dough in a greased bowl, cover, and let it rise in a warm spot until doubled, about 1 to 1 1/2 hours.
- Make the filling: Stir the softened butter, brown sugar, and cinnamon together into a smooth, spreadable paste.
- Roll out: Grease a 9×13-inch baking pan. Punch down the dough and roll it out on a lightly floured surface into a 16×12-inch rectangle.
- Fill and roll: Spread the filling evenly over the dough, leaving a 1/2-inch border along one long edge. Starting from the opposite long edge, roll the dough up tightly and pinch the seam closed.
- Slice: Cut the log into 12 even rolls with a serrated knife, using a gentle sawing motion so the rolls keep their round shape. For even sizes, cut the log in half, then each half in half, then each quarter into thirds. Arrange the rolls cut side up in the pan.
- Chill: Cover the pan tightly with plastic wrap and refrigerate for 8 to 16 hours.
In the Morning
10. Second rise: Take the pan out of the fridge and let the rolls sit, still covered, in a warm spot for 1 to 1 1/2 hours, until puffy and touching each other. Preheat the oven to 350°F (175°C) during the last 20 to 30 minutes.
11. Bake: Bake for 25 to 30 minutes, until golden brown and the center roll reads 190°F on an instant-read thermometer. If the tops brown too quickly, tent loosely with foil.
12. Make the frosting: While the rolls bake, beat the cream cheese and butter until smooth. Add the powdered sugar, vanilla, and salt, and beat until fluffy. If it’s too thick to spread, beat in the milk.
13. Frost and serve: Let the rolls cool for 5 to 10 minutes, then spread the frosting over them while they’re still warm so it melts into every swirl.