Heat the water to between 105°F and 115°F. Add a pinch of sugar and the yeast. Stir briefly and then set aside for the yeast to activate. When the yeast is bubbly and risen, after about 5 minutes, proceed with the recipe.
n the bowl of a stand mixer fitted with a dough hook, combine the warm milk, melted butter, eggs, sugar, and the yeast mixture. Stir together and then add the flour and salt.
Mix, using the dough hook, until the dough starts to come together. Scrape down the sides occasionally to encourage the dough to come together. If the dough is too sticky and sticks to the side without forming a ball, then add more flour, a tablespoon at a time.
Continue mixing with a dough hook on low speed for about 5 minutes until the dough is soft and stretchy, dusting with flour as needed. After mixing, take the dough out and lightly knead a couple of times on the counter to bring it together into a smooth ball.
Transfer the dough to a greased bowl. Rub a little oil on top of the dough. Cover with cling film or a tea towel and then set in a warm place to rise for 1 to 1 1/2 hours until double in size.
Chestnut Purée
Combine the roasted chestnuts and milk in a saucepan. Add the brown sugar and bring to a simmer. Turn the heat to medium low and simmer the chestnuts for about 15 minutes until softened and the milk has reduced somewhat. Keep an eye on the saucepan while simmering as milk has a tendency to boil over if it gets too hot.
Remove the chestnuts from the heat and transfer to a food processor along with some of the milk. Add the vanilla paste and kosher salt. Blend until a smooth paste, stopping to scrape down the sides occasionally and adding as much of the warm milk as needed to make a smooth, spreadable purée. You may need to add some additional milk to achieve the correct consistency. The texture should be similar to buttercream frosting. Transfer the chestnut purée to a bowl and let cool before using.
Cinnamon Filling
In a small bowl, combine the softened butter, brown sugar, and cinnamon. Blend together using a spatula until fully combined.
Assemble the rolls
After the dough has risen, punch it down to deflate completely. Transfer the dough to a lightly floured counter. Roll the dough out into a large rectangle, about 18” by 10” in size. Spread the cinnamon filling over the dough.
Set aside 1/4 cup of the chestnut purée to use in the cream cheese icing. Drop the remaining chestnut purée in dollops over the cinnamon filling and gently spread it out evenly. Spray a 9” by 13” baking pan with non-stick spray. Roll the dough up starting with the long side. Use a sharp knife to cut the roll into 12 pieces. Place the rolls in the prepared pan. Cover with a tea towel and let rise for another 30 minutes or until double in size.
Chestnut Cream Cheese Icing
In a stand mixer fitted with a paddle attachment, combine the reserved 1/4 cup chestnut purée, softened butter, and cream cheese. Beat together until creamy. Add the icing sugar and beat until combined.
Bake the rolls
Preheat the oven to 350°F. Bake the cinnamon rolls for 25 to 35 minutes until lightly browned and cooked through. When the rolls are done, transfer the baking dish to a rack and let sit for a few minutes. Drop the icing onto the warm rolls and let sit for a minute to soften. Gently spread the icing over the rolls. Enjoy!