In the bowl of a stand mixer, using the paddle attachment, combine 5 cups flour, sugar, yeast, and salt.
In saucepan or microwave-safe dish, heat water and shortening until warm (120° – 130°).
Add liquids to flour mixture. Add eggs. Blend at low speed until moistened. Beat 4 minutes at medium speed.
Switch to the dough hook and mix in the remaining flour a little at a time, to make a soft dough, add more or less flour as needed. Knead the dough for 5 minutes until smooth and elastic. Place dough in a lightly oiled bowl and turn to grease top. Cover; let rise in a warm place until double about 30 minutes.
Grease tw 9x13-inch pans with nonstick cooking spray and set aside.
Divide dough in half. With a rolling pin, roll one half of the dough into a rectangular shape, about 22 X 13 inches. Spread dough evenly with half of the softened butter. Sprinkle dough with half of the brown sugar, cinnamon, and raisins.
Starting from one of the long sides of the rectangle, roll the dough into a log. Using a piece of unflavored dental floss, cut the log into 12 rolls about 1 ½ inches thick. Place rolls in greased 9X13 baking pans. Repeat with the other half of the dough and filling. Allow the rolls to rise, covered, until they've doubled in size 30 minutes to 1 hour.
Preheat oven to 350°F. Bake for 28-32 minutes or until cinnamon rolls are golden brown on top and cooked in the middle. The internal temperature of the rolls should be 190–200°F. 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, powdered sugar, milk, and vanilla. Frost the cooled cinnamon rolls generously!