In a stand mixer fitted with the dough hook attachment, combine the lukewarm water, yeast, and sugar. Allow to proof for 10 minutes.
Meanwhile, gently heat the butter and milk until lukewarm, about 110F. You can do this in a small saucepan on the stovetop or in a microwave safe dish in the microwave. Note: Be sure the mixture is cooled to lukewarm: warm to the touch but not hot, before adding to the other ingredients or you can kill the yeast. Check the temperature with a kitchen thermometer if you're not sure.
Add the milk and butter mixture along with the vanilla to the yeast mixture. Add the salt and mix briefly to combine.
Add the flour, and mix slowly until a shaggy dough forms. Allow the machine to continue kneading the dough for another 2 minutes on low speed.
Transfer dough to a lightly oiled bowl, and cover tightly. Allow the dough to rise in a warm spot for 25 minutes.
While the dough is rising, make the cinnamon filling. Melt the butter in a small bowl in the microwave. Mix in the sugar, flour, cinnamon, and salt. You should have a thick paste-like consistency.
When it is done rising, remove the dough to a lightly floured surface and gently pat into a rectangle about 8 x 10 inches.
Use a spoon to dot the cinnamon filling evenly over the dough and then spread it out into an even layer. You don't need to be completely perfect, just get it as even as you can, all the way to the edges.
Using a pizza cutter or a sharp knife, slice the rectangle in half lengthwise, and then do the same for each half. You should have four long, narrow strips of dough.
Take one strip and roll it up like you would make a single cinnamon roll. Place this in the center of your prepared pie plate or skillet.
Next, take another strip of dough (handle it gently so it doesn't stretch out too much), and continue to wrap around the first spiral of dough. Pinch the two ends together where they meet. Repeat for the other two strips of dough, continuing to wind around for one "giant" cinnamon roll.
Don't worry if your cinnamon roll looks a little wonky or doesn't fill up the pie plate. The dough will expand a bit more during the second rise, and while it bakes. Plus, once you cover the whole thing in glaze, no one will be looking at the details!
At this point you can let the dough rise in a warm spot for another 25 minutes. Or you can cover the unbaked cinnamon roll tightly in plastic wrap and set in the fridge to rise overnight.
If you've left the dough to rise in the fridge overnight, take it out for about 30 minutes to come to room temperature before baking.
Preheat oven to 400F. Bake the cinnamon roll for 25-35 minutes until golden brown. If it looks like it's getting too brown on top, cover loosely with a piece of tinfoil.
Remove from the oven and allow to cool partially before glazing.
To make the glaze, first melt the butter (I do this in a small bowl in the microwave). Combine the melted butter, powdered sugar, milk, and vanilla extract in a bowl and whisk well until smooth. Pour evenly over the warm cinnamon roll and spread out with a spoon or an offset spatula.
Enjoy warm or allow the glaze to set and the cinnamon roll to cool before slicing and serving.
Notes
For a more 'flooded' look on the top of your giant cinnamon roll feel free to increase the glaze amount.
Nutritional information is provided as a courtesy and is an estimate only. This information comes from online calculators. Although The View from Great Island attempts to provide accurate nutritional information, these figures are only estimates.
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