Activate the yeast: In a large bowl (or stand mixer bowl), whisk together the warm milk and granulated sugar. Sprinkle in the yeast and let stand for about 5 minutes, until foamy.
Add the wet ingredients: Stir in the pumpkin puree, melted butter, egg, pumpkin pie spice, and salt until smooth.
Make the dough: Add the flour gradually and mix until a soft dough forms and starts pulling away from the sides. Knead 5–8 minutes (dough hook or by hand) until smooth and elastic. If overly sticky, add 1–2 tablespoons flour as needed.
First rise: Place dough in a lightly greased bowl, cover, and let rise in a warm spot until doubled, about 60–90 minutes.
Roll out: On a lightly floured surface, roll dough into a large rectangle about 1/4-inch thick.
Fill: Spread the softened butter evenly over the dough. Mix brown sugar, cinnamon, and pumpkin spice, then sprinkle evenly over the butter. Add pecans and/or dried cranberries if using.
Shape: Roll up tightly from the long side into a log. Slice into 12 even rolls using a sharp knife or dental floss.
Second rise: Arrange rolls in a greased (or parchment-lined) 9x13-inch baking dish. Cover and let rise 30 minutes, until puffy.
Bake: Heat oven to 350°F (175°C). Bake 25–30 minutes, until golden and cooked through.
Make the frosting: Beat softened cream cheese with powdered sugar, milk, and vanilla until smooth and spreadable. Add a splash more milk if needed.
Finish: Spread frosting over warm rolls, then drizzle with chocolate sauce and caramel sauce if desired. Serve warm.