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To make the dough: Weigh your flour; or measure it by gently spooning it into a cup, then sweeping off any excess.
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In the bowl of a stand mixer fitted with the dough hook, mix together all the dough ingredients except the butter on medium-low speed to make a smooth, stretchy dough. After 7 to 10 minutes, it should clean the sides of the bowl.
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Once the dough has developed some strength and elasticity, add 1 or 2 tablespoons of the butter and mix on medium speed until it’s fully incorporated into the dough, about 1 to 2 minutes. Scrape the sides of the bowl if necessary, then continue adding the butter a couple of tablespoons at a time, mixing to incorporate fully before adding the next piece. Continue this process until all of the butter has been fully incorporated and the dough has formed a soft, smooth ball, about 8 to 12 minutes total. (We don't recommend trying to knead this dough by hand.)
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Form the soft dough into a ball, place it in a greased bowl, cover, and let rise for 1 hour at room temperature. Then refrigerate the dough for at least 3 hours, or overnight. This will slow the fermentation and chill the butter, making the dough easier to handle.
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To make the filling: Just before you are ready to assemble the giant cinnamon roll, in a small bowl, stir together the brown sugar, flour, cinnamon, and salt.
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Add the melted butter, water, and vanilla and stir until smooth.
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To assemble the giant cinnamon roll: Transfer the dough to a lightly floured surface or a rolling mat and divide in half (about 475g each).
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Line a well-seasoned cast iron skillet that’s 10" to 11" in diameter across the top and about 9" across the bottom with a parchment round, then lightly grease the sides of the pan. You can also use a 9" springform pan, or a 9" or 10" cake round that’s at least 2" tall. Place the pan on a parchment-lined baking sheet.
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Roll out each piece of dough into a 9" x 13" rectangle. Divide the filling evenly over each half of the dough, using about 1/3 cup (125g) filling per rectangle. Spread evenly over the entire piece of dough all the way to the edges. (A small offset spatula is a helpful tool here.)
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Gently pick up one of the filling-covered rectangles and place it directly on top of the second rectangle. You will now have a stack of dough/filling/dough/filling.
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Use a pizza cutter or bench knife to cut the stacked dough the long way into 1 1/2" strips, resulting in 6 strips that measure 1 1/2" x 13" each.
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Starting at the end of one of the strips, loosely roll it up into a coil (as if you were rolling one cinnamon roll) and place it in the center of the prepared pan with the swirl side up. This is the center of the giant cinnamon roll.
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Cut the remaining 5 strips in half crosswise, resulting in 10 strips that measure 1 1/2" x 6 1/2" each.
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Working with one strip at a time, pick it up and wind it around the center of the cinnamon roll, starting each strip at the end of the previous one. Continue assembling this way until you have used all 10 strips. Be careful not to coil too tightly; leave some room between the rings for the dough to expand.
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Cover the shaped cinnamon roll and let rise for 60 to 75 minutes, until puffy.
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Towards the end of the rise time, preheat the oven to 350°F.
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Bake for 50 to 55 minutes, tenting with foil after 35 minutes. The giant cinnamon roll should be deep golden brown and the internal temperature at the center should be 190°F when measured with a digital thermometer.
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To make the glaze: While the giant cinnamon roll is cooling, in a small bowl, stir together the confectioners’ sugar, vanilla, and milk or water.
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Drizzle the glaze over the cinnamon roll while it's warm from the oven and serve immediately.
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Storage information: Store any leftovers, well covered, at room temperature for several days; freeze for longer storage.
