In a medium-sized sauté pan over medium heat, add Bacon (1 pound) and cook, stirring occasionally, until the bacon is browned and crispy. Remove from the pan with a slotted spoon and place on a paper towel to drain. Reserve 2 Tablespoons of the bacon grease from the pan for use in the frosting later.
In a large bowl or in the bowl of a stand mixer, add Water (2 cup), Active Dry Yeast (4 teaspoon), and Granulated Sugar (2/3 cup). Let sit for approximately 5 minutes, until the yeast starts to get foamy.
Add in Egg (2), Kosher Salt (1 1/2 teaspoon), and All-Purpose Flour (6 cup). Mix ingredients together on low if using a stand mixer or mix by hand with a wooden spoon. If using a stand mixer, speed can be increased to medium once the flour is mostly incorporated.
Once all of the ingredients are mixed together, slowly add in the remaining All-Purpose Flour (2 cup), ½ cup at a time until the dough pulls away from the sides of the bowl.
Once the dough forms a ball, turn it out onto a floured surface and begin to knead. Add in more flour as needed until the dough no longer sticks to your hands. Continue kneading the dough until it is smooth and elastic. Kneading can be done completely in the stand mixer as well.
Grease a large bowl with baking spray or butter and place kneaded dough into it. Cover with a towel or plastic wrap and let sit in a warm place until doubled in size, approximately 1 hour.
Once the dough has risen to double in size, punch down the dough and remove it from the bowl. Place on a floured surface and roll out into a large rectangle that is approximately 10x25 inches.
Spread the surface of the dough evenly with Unsalted Butter (1 stick) and then sprinkle the butter with the Brown Sugar (1 cup). Sprinkle half of the cooked bacon on top of the brown sugar and reserve the other half for later use.
Starting on the long side of the cinnamon rolls, tightly roll up the dough. Using a serrated knife, cut the roll into 24 equal pieces.
Line two baking sheets with baking mats or parchment paper and lay the cut rolls evenly spaced on the baking sheets with the cut side facing up. Cover the rolls with a towel or plastic wrap and let rise in a warm spot until doubled in size, approximately 1 hour.
While rolls are rising for the second time, combine Powdered Confectioners Sugar (4 cup), Pure Maple Syrup (1/3 cup), Whole Milk (1/3 cup), and reserved bacon grease in a medium-sized bowl. Using a whisk, mix ingredients until thoroughly combined. Set aside.
Preheat oven to 350 degrees F (180 degrees C).
Once the rolls have doubled in size bake in the preheated oven for 25-30 minutes until filling is bubbly and rolls are slightly browned.
Remove from the oven and let cool for 15 minutes. Once rolls have cooled slightly, spread frosting evenly over all of the rolls and sprinkle with the remaining cooked bacon pieces.