Cup of Yum
1. In a small bowl, gently stir warm water with yeast and 1 tsp sugar. Set aside for 10 minutes until the yeast is foamy.
2. Pour the milk into a saucepan and place it over over medium-high heat, whisking to ensure the milk doesn't burn at the bottom. The milk will start to steam lightly and bubble around the edges after a minute or two. Once the milk starts to bubble (don't let it boil!) remove it from the heat.
3. Put the 1/3 cup of sugar, shortening, and salt into the bowl of a stand mixer. Pour scalded milk on top and whisk until well combined. Allow to cool until no longer hot, until about 110 degrees F.
4. Once the milk mixture has cooled, stir two cups of flour in using the dough hook attachment on a stand mixer. Add the yeast mixture and mix until well combined, then mix in the egg and vanilla.
5. Mix in 2 more cups 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 8-10 minutes until the dough is smooth, elastic, and no longer sticking to the sides of the bowl, adding a little extra flour if needed.
6. Once the dough is kneaded, place it into a lightly oiled bowl. Cover with plastic wrap and allow to rise in a warm place for about 1 1/2 hours or until doubled in size.
7. Once doubled in size, punch down the dough and roll it out on a lightly floured work surface into a large rectangle. The dough should be about 1/4 inch thick or about 12x18 inch rectangle.
8. Spread the softened butter all over the dough, leaving an inch around the edges bare. Mix the brown sugar and ground cinnamon in a mixing bowl until well combined, then sprinkle generously over the butter.
9. Roll the dough up tightly, starting at the widest side. Cut the roll of dough into 12 equal pieces and place each piece in a greased 9x13 baking pan or two greased 9 inch pie dish. Cover with plastic wrap and allow to rise in a warm place for about 45 minutes.
10. Preheat oven to 375 degrees F.
11. Place cinnamon rolls in the oven and bake for about 25 minutes or until the cinnamon rolls are cooked through. Cover loosely with foil after about 10-15 minutes to prevent too much browning.
12. Once the cinnamon rolls are done, remove from oven and set aside to cool for 10 minutes.

To make the cream cheese icing:

1. In a medium-sized mixing bowl, whisk the cream cheese and butter together until smooth. Mix in the powdered sugar and vanilla extract until fully combined. Then mix in the milk, adding more as needed until it is somewhat pourable.
2. Once the cinnamon rolls have cooled slightly, frost them, serve and enjoy!
3. Store frosted cinnamon rolls in the refrigerator covered tightly for 3-4 days and reheat in the microwave.
4. To make ahead of time: Cinnamon rolls may be baked, cooled, and covered tightly at room temperature for up to 2 days. Add the cream cheese icing right before serving.