Add the warm water, brown sugar, and yeast to a large bowl. Set the bowl aside for 5 minutes, or until the yeast has bloomed. If the yeast doesn’t bloom, discard it and begin with fresh yeast.
Add the melted butter, molasses, egg, and vanilla and whisk to combine.
Using a dough whisk or wooden spoon, slowly mix in the flour. Mix just until the dough forms into a shaggy ball. You may not need the full 5 cups - use any extra flour to dust your work surface while kneading.
Once a shaggy dough has formed, transfer the dough to a lightly floured surface and knead for 2-3 minutes, or until a smooth dough has formed.
Place the dough in a lightly oiled bowl and set it aside to rise until doubled in size, about 1.5 hours.
Prepare the filling (below) while the dough rises.
Once the dough has risen, punch it down and roll it out to a 1/2 inch thick rectangle.
Spread the filling over the dough, making sure to spread it all the way to the edges.
Roll the dough into a tight log, making sure to pinch the seam together so it doesn’t unroll in the oven.
Slice the log into 8 (approximately 1-1/2 inch) rolls.
Grease a 9x13 baking dish with butter or non-stick baking spray.
Add the rolls to the pan and set the pan aside to rise in a warm place until the rolls fill the pan, about 15 minutes.
While the rolls rise, preheat your oven to 350 degrees F.
After the rolls have doubled in size, bake them for 30 minutes, or until the tops are golden brown.
While the rolls bake, prepare the cream cheese frosting (below).