Into the bowl of a stand mixer fitted with a paddle attachment, add Bread Flour (2 1/2 cup), Instant Dry Yeast (1 tablespoon), Salt (1 teaspoon), and Granulated Sugar (1/4 cup). Mix to combine.
Add Vegetable Oil (1/4 cup), Buttermilk (1 1/4 cup), and Vanilla Extract (2 teaspoon). Mix to combine, about 2 minutes on medium-high speed.
Switch from paddle attachment to dough hook. Add remaining Bread Flour (1 cup). Mix until dough is no longer sticking to the sides of the bowl, adding more flour as needed.
Mix for an additional 5 minutes. Dough should not stick to your fingers.
Turn dough out onto a lightly floured surface and knead a few times. Let it sit as you make your cinnamon mixture.
Into a mixing bowl, add Brown Sugar (1/3 cup) and Ground Cinnamon (2 tablespoon). Mix to combine.
Roll the dough out into a 14 by 12-inch rectangle, about 1/4-inch thick.
Spread dough with Butter (3 tablespoon), followed by brown sugar and cinnamon mixture.
Roll the dough up into a log. Cut into 12 even rolls.
Lay the rolls out on a baking sheet. Drizzle them with a mixture of Unsalted Butter (1/2 cup) and Ground Cinnamon (3 teaspoon). Brush to coat evenly.
Cover with plastic wrap and let rest for 1 hour.
Preheat oven to 350 degrees F (176 degrees C).
Bake for 20-25 minutes.
Allow rolls to cool for 45 minutes before topping with glaze.
To make the glaze, stir together Powdered Confectioners Sugar (3 1/2 cup) and Vanilla Extract (1/2 tablespoon). Add the Milk (3 tablespoon) a bit at a time, whisking until smooth. Pour over the rolls.
Serve and enjoy! They are best if warmed up for a few seconds in the microwave.