Add yeast to 1 cup of lukewarm water and add the sugar. Set aside for about five minutes.
In the bowl of a stand mixer, add shortening, sugar, and salt to the 1/2 cup of hot water and beat for 30 seconds, using the beater blade. Let cool to lukewarm temperature.
Stir in 2 cups of flour and mix until smooth. Add yeast mixture and mix until well combined. Mix in the beaten eggs.
Gradually stir in the remaining flour and mix with the dough hook for about 7 minutes. Dough should come away from the sides and making a slapping sound. You may need more flour if the dough is sticky.
Cover and let rise for 30 minutes. After the dough has doubled in size, remove it from the bowl.
With a rolling pin, roll the dough into a rectangular shape, about 22 X 13 inches.
Spread dough evenly with softened butter and sprinkle dough with half of the brown sugar, raisins, and cinnamon.
Roll up dough into one long roll. Cut rolls, using a piece of dental floss or thread, about two inches thick. Place rolls in greased 9X13 baking pans.
Let the rolls rise until double in bulk. If you are doing the rolls for the next day stop here.
Preheat oven to 350 degrees F. Bake for 20-30 minutes or until cinnamon rolls are golden brown on top and cooked in the middle.
Remove from the oven and let the rolls cool to room temperature.
While the rolls are cooling, make the frosting. In a medium bowl, whisk together butter, sugar, milk, and vanilla. Frost the cooled cinnamon rolls generously!
For Overnight Rolls:
Cover with plastic wrap and refrigerate overnight.
In the morning, pull the rolls out and let them come to room temperature and rise a little – about 30 mins.