Warm the milk to about 105–110°F. Stir in the yeast and a teaspoon of sugar, let it sit 5–7 minutes until foamy. In a large bowl, whisk pumpkin, melted butter, sugars, egg, salt, and spices, then add the foamy yeast mixture.
Gradually add 3 cups flour and mix until a shaggy dough forms. Knead on a floured surface, adding remaining flour as needed, until smooth and slightly tacky (6–8 minutes) or use a stand mixer with a dough hook.
Place dough in an oiled bowl, cover, and let rise in a warm spot until doubled, about 60–90 minutes.
Roll dough into a 12x18-inch rectangle. Spread softened butter, sprinkle filling mixture evenly, add nuts if desired. Roll tightly from the long side and seal the seam.
Cut the log into 12 even rolls and place in a greased 9x13-inch pan. Cover and let rise 30–45 minutes until puffy.
Preheat oven to 350°F (175°C). Bake 22–28 minutes until golden and set. Tent with foil if tops brown too quickly.
Whisk powdered sugar, milk, vanilla, and salt until smooth. Drizzle over warm rolls and serve slightly warm.