Whisk the warm water with the teaspoon of sugar until the sugar is dissolved. Sprinkle the yeast on top and gently stir it into the water. Set aside for 5-10 minutes until the yeast is foamy.
Add the 5 tablespoons of sugar, shortening, and salt to a heat-proof mixing bowl or the bowl of a stand mixer. Pour the scalded milk on top and whisk until well combined. Set aside and allow to cool until it's warm and no longer hot (about 110°F).
Once the scalded milk mixture has cooled, mix in 2 cups (250 grams) of flour by hand or using the dough hook attachment on a stand mixer. Add the yeast mixture and mix until well combined, then mix in the egg.
Mix in 2 more cups (250 grams) of flour until fully combined, then mix in 1-2 tablespoons of flour at a time until the dough is easy to handle. Knead the dough by hand on a lightly floured surface or using the dough hook on a stand mixer on low speed for 5-10 minutes until the dough is smooth and elastic, adding a little extra flour if needed.
Once the dough is kneaded, form it into a ball and place it into a lightly greased bowl. Cover and allow to rise in a warm place for about 1 hour or until double in size.
Once double in size, punch down the dough and roll it out on a lightly floured surface into a large rectangle. The dough should be about 1/4-inch thick or about a 12x18 inch rectangle.
Spread the softened butter all over the dough. Mix the brown sugar and ground cinnamon in a mixing bowl until well combined, then sprinkle on top of the butter and gently press it down.
Starting at the 18-inch side, roll the dough up tightly. Cut the roll of dough into 12 equal pieces and place each piece in a greased 9x13 baking pan. Cover and allow to rise in a warm place for about 45 minutes.
After about 30 minutes of rising, preheat the oven to 375°F. Once the oven is preheated, place the cinnamon rolls in the oven and bake at 375°F for about 25 minutes or until the cinnamon rolls are cooked through in the center. Cover loosely with foil after about 10-15 minutes of baking to prevent excess browning. Once the cinnamon rolls are done, remove from the oven and set aside to cool.