To make the dough, heat the milk to 110 degrees. Pour the milk to the bowl of an electric stand mixer, fitted with the hook attachment. Add the 1/2 teaspoon of sugar to the milk, mix to combine. Add yeast. Mix. Let rest for 5 minutes until the yeast is foamy.

Add all the remaining dough ingredients EXCEPT the butter. Mix on low until combined. Knead for a minute or two until a sticky dough forms. Add in the butter and knead on medium until combined. Knead on medium/high for another minute or two until smooth and silky.

Transfer to another greased bowl and let rise for 1 and a half hours until doubled in size.

While the dough rises, make the glaze. In a small pot, combine sugar, stout, and vanilla. Whisk to combine. Bring to a simmer over low and let simmer for 20-25 minutes until reduced by half. Transfer to a heat safe container and let cool.

Make the filling. Add all the ingredients for the filling to a bowl and mix to combine.

Roll out the risen dough on a well floured surface into a 10x20 inch rectangle. Spread the filling all over the dough, leaving a one inch border.

Roll the dough towards you into a long jelly roll. Cut into 16 slices/rolls. Transfer to a greased 9x13-inch pan. Let rise for 1 1/2 hours, while the oven preheats.

Preheat the oven to 375 degrees F.

Bake the rolls for 30 minutes. Take the rolls out and glaze with the stout syrup every 10 minutes.

Make the glaze. Whisk together the buttermilk and powdered sugar. Cook bacon, pat off excess grease, and chop.

Once the cinnamon rolls come out of the oven, let cool for 7-10 minutes in the pan before topping with icing, bacon, and a few spoonfuls of more glaze.