In a small saucepan over medium low heat, warm the milk to 110°F or lukewarm. Once the milk is warm, pour it into the bowl of a stand mixer.
Add the sugar into the milk and stir until the sugar is dissolved.
Sprinkle active dry yeast on top and slightly stir. Let the yeast sit and bloom, about 5 minutes. After 5 minutes the yeast should look frothy and puffed, if it doesn’t your yeast might be dead. It is best to start over with new milk, and new yeast.
Once the yeast has bloomed add the butter, eggs, and 3 cups of flour. Using the dough hook attachment (or with a sturdy wooden spoon if you’re not using a mixer) and mix until a sticky dough has formed.
Gradually add another 3 cups of flour until a soft dough has formed. The dough will still look slightly sticky, but it will be firm enough to pull away from the sides of the mixing bowl.
On a large lightly floured surface knead the dough for 3-5 minutes adding small amounts of flour as needed. When the dough is done, it will spring back when lightly poked.
Lightly grease a large bowl with the extra virgin olive oil. Add the dough ball, turning over to completely coat it and tightly cover the bowl with plastic wrap or a bowl cover. Place in a warm space and let the dough rise for 1 hour, or until doubled in size.
Once dough has risen and roughly doubled in size, remove the plastic wrap and punch the dough down.
Turn the dough onto a large lightly floured surface and divide into two pieces.
Using a rolling pin, roll the dough into a rectangle that is approximately 20"x14". Dough should be about ¼” thick.
Use a spatula or an offset spatula to spread half of the vanilla butter mixture onto the dough.
Sprinkle half of the cinnamon sugar filling mixture on top of the vanilla butter layer, making sure to cover the entire surface.
Starting on a long side, roll the dough up tightly. Place it seam side down.
Repeat the above steps with the second piece of dough to make a second cinnamon roll log.
Lightly butter two 9”x13” oven safe dishes and set aside.
Trim off the ends of each log and mark each into 8 even pieces. Cut using a sharp knife, bench scraper, or kitchen twine.
Place cinnamon rolls in the buttered baking dishes, 8 per dish. They can sit close together.
Cover the baking dishes loosely with plastic wrap and place in a warm area to let rise another 30 minutes.
Preheat the oven to 350°F
After the rolls have finished the second rise, remove the plastic wrap and bake for 20-25 minutes or until golden brown.
Let the cinnamon rolls cool until just slightly warm to the touch, and then using the back of a spoon, spread generously with cream cheese frosting.
Cinnamon Sugar Filling
In a medium sized bowl, combine the brown sugar, white sugar, and cinnamon. Using a fork, combine, taking care to break up any large clumps of brown sugar. Set aside.
Vanilla Butter Filling
In a small bowl, combine the softened butter, vanilla, and ¼ cup of the above dry filling. Using a hand mixer or stand mixer fitted with a paddle attachment, beat on medium high until fully combined. Set aside.
Cream Cheese Frosting
In a large bowl with a hand mixer or in the bowl of a stand mixer fitted with the whisk attachment combine the cream cheese, butter, powdered sugar, vanilla and salt. Mix until velvety smooth. Cover and set aside.
Notes
If you notice that your yeast is not getting frothy, it could mean that the yeast is "dead". Before continuing with the recipe, remake the yeast portion until you have frothy yeast. One of the first culprits of killing yeast is that the milk is too warm.
Sift the all purpose flour through a fine mesh sieve to ensure there are no lumps in your dough.
Please Note- The nutritional information provided is an estimate based on an online nutrition calculator and it will vary based on the ingredients that you use.