Activate Yeast: In a small bowl, combine warm milk and yeast. Let sit 5 minutes until foamy.
Make Dough: In a large bowl, mix pumpkin puree, sugar, melted butter, egg, salt, and pumpkin pie spice. Add yeast mixture. Gradually stir in flour until dough forms.
Knead: Transfer to a floured surface and knead for 6–8 minutes until smooth and elastic. Place dough in a greased bowl, cover, and let rise 1 hour or until doubled in size.
Prepare Filling: Mix brown sugar, cinnamon, softened butter, and pumpkin puree in a small bowl.
Roll Out Dough: Punch down dough and roll into a rectangle (about 14x10 inches). Spread filling evenly.
Shape Rolls: Roll up tightly from the long side. Slice into 12 even pieces and place in a greased baking dish. Cover and let rise another 30 minutes.
Bake: Preheat oven to 350°F. Bake rolls for 25 minutes until golden brown.