Melt 1 c. sugar in heavy skillet over low heat, stirring constantly. Heat until melted to a golden brown syrup, stirring constantly. Remove from heat. Add boiling water & stir over low heat until lumps are dissolved. Pour into measuring cup ¼ c. of caramel mixture & add enough cold water to make 1 c. of liquid.
Cream together the softened shortening & remaining sugar until fluffy. Beat in thoroughly eggs. Sift together the flour, baking powder, & 1 tsp. salt. Stir in alternately with caramel mixture. Pour into two 9" layer pans or 13"x9" oblong pan & bake 35 minutes in preheated 350°F oven.
Heat together remaining caramel mixture, cream, & butter to make the burnt sugar frosting. Beat in the powdered sugar, salt, & vanilla extract.
Cream the shortening, water & sugar together until light & fluffy. Add the molasses & egg yolk & mix until well blended.
In a separate bowl, whisk together all the dry ingredients. Gradually add the dry ingredients to the wet mixture. If using a stand mixer, use stir. The dough will be sticky.
DO NOT ADD MORE FLOUR REGARDLESS OF HOW TEMPTED YOU MAY BE!!! Too much flour will make the cookies tough. Form into 2 flat disks & put in the freezer for at least an hour or more.
Preheat oven to 350°F.
When the dough is cold enough to handle, roll it to about ¼” thick between 2 pieces of wax paper (the wax paper keeps you from having to use more flour). I roll mine a little thinner because I like a little crispness on the edges.
Gently press together the scraps into another disk & put back in the freezer until ready for use. Bake for 8-10 minutes on parchment lined cookie sheets. Cool on pan for about 5 minutes before transferring to a cooling rack. Cool completely before decorating.
Chef’s Note: I use shortening instead of butter or margarine because shortening is flavorless and doesn’t impact the spices. I think butter is best served in sugar cookies. If you decide to substitute butter or margarine for the shortening, omit the water from the recipe.