Whisk together 2 3/4 cups of all-purpose flour, 2 tablespoons granulated sugar,1/2 teaspoon kosher salt, and 1 package of yeast.
In a microwave-safe bowl, heat ¾ cup milk and 3 tablespoons of butter on 50% power. Remove after 1 1/2 minutes or when the butter is mostly melted.
Give the butter mixture a stir and allow the butter to finish melting. Then, let the mixture cool slightly before adding it to the dry ingredients.
To the mixture, add 1 large egg and one large egg yolk and mix with a spatula until a dough forms.
Knead the dough with your hands for 5-6 minutes.
Spray the dough with non-stick cooking spray and set aside.
Place 5 tablespoons softened butter, 2 teaspoons cinnamon, and 1/3 cup brown sugar in a small bowl. Mix until a smooth paste forms.
Roll the dough on a floured surface into a 9x14-inch rectangle.
Spread the filling evenly across the dough.
Rolling from the long end, roll the dough into a log.
Using a serrated knife, slice the log into 12 slices. To do this, slice the log in half. Slice each half into thirds. Then slice each of these sections in half.
Line a baking sheet with parchment paper.
In roughly the middle of the sheet, create a pyramid. Arrange a row of four slices. Above the four slices, arrange a row of three slices, then a row of two, then a row of one.
Create the trunk of the tree by placing the remaining two slices below the pyramid.
Spray with non-stick cooking spray and cover with plastic wrap.
Set aside for 75-90 minutes, or until the rolls have grown nearly double in size.
Preheat the oven to 375ºF. Bake for 18-20 minutes.
Remove rolls from the oven and allow to cool slightly.
Whisk together 1 cup powdered sugar, 1 teaspoon vanilla, and 2 tablespoons of water until smooth.
Place the icing in a plastic bag and snip off one corner of the bag. Glaze the rolls.
Add sprinkles and other decorations. Enjoy!