Start by generously buttering a 1-inch (2.5 cm) cast-iron skillet or cake pan—don’t be shy with it! You want that roll to lift out easily later.
In a large bowl, whisk together the warm milk, melted butter, and granulated sugar. The mixture should feel pleasantly warm to the touch, around 100–110˚F (40˚C). If it’s too hot, give it a few minutes to cool down so it doesn’t harm the yeast.
Sprinkle the yeast evenly over the warm mixture and let it sit for about a minute to wake it up. Now, add 4 cups of flour and stir it in using a wooden spoon until it’s just combined. Cover the bowl with a clean towel or plastic wrap and place it somewhere cozy to rise for 1 hour.
After an hour, your dough should be puffed up and nearly doubled in size. Take off the cover and stir in another ¾ cup (95 g) of flour along with the baking powder and salt. Mix everything well, then turn the dough out onto a floured surface.
Gently knead the dough, adding a bit more flour if needed, until it’s soft, smooth, and no longer sticking to your hands or the counter.
Roll the dough into a big rectangle, about ½ inch (1.5 cm) thick. Take a moment to square off the corners so your roll will look nice and even.
For the filling, mix together the softened butter, light brown sugar, and cinnamon in a small bowl. Spread this sweet, buttery mix all over your rectangle of dough, going right up to the edges for maximum cinnamon-sugar goodness.
Using a pizza cutter, slice the dough into 4 long, even strips by making 3 horizontal cuts. Start at the top and roll the first strip from right to left. Once you have a roll, place it on the end of the next strip and keep rolling. Keep stacking and rolling until you’ve built one giant cinnamon roll!
Gently place your cinnamon roll into the prepared skillet or pan and cover it with plastic wrap. Let it rest in a warm spot for about 30 minutes. It should puff up nicely and fill the pan during this time.
Preheat your oven to 325˚F (160˚C).
Once your roll has risen, remove the plastic and bake for 45 minutes. Then cover it loosely with foil to keep it from browning too much and bake for another 35 minutes.
While it’s baking, whip up the frosting! In a medium bowl, whisk together the cream cheese, butter, milk, vanilla, and powdered sugar until it’s smooth and dreamy.
After baking, let the giant cinnamon roll cool in the pan for at least 20 minutes. Then carefully remove it, drizzle with that creamy frosting, and get ready to dig in.
Enjoy every gooey, warm, cinnamon-filled bite!