Combine flour, granulated sugar, yeast, and salt in a large mixing bowl. Warm the pumpkin puree, milk, and melted butter to 110°F and stir in the egg. Pour the wet mixture into the dry ingredients and knead for 8–10 minutes until the dough becomes smooth and elastic. Transfer to a greased bowl, cover with plastic wrap, and let rise for 1 hour until doubled in size.

While dough rises, prepare your filling by mixing packed brown sugar and ground cinnamon in a small bowl. This pumpkin cinnamon rolls filling will distribute evenly across the rolled dough without clumping. Set aside and keep the softened butter nearby for spreading. The combination should smell warm and distinctly autumnal.

Punch down the risen dough and transfer to a floured work surface. Roll into a 16x12 inch rectangle, working gently to maintain even thickness throughout the sheet. Spread the 2 tbsp softened butter across the entire surface, leaving a small margin at the top edge.

Sprinkle the cinnamon-sugar filling evenly across the buttered dough, pressing gently so it adheres. Roll the dough tightly from the long side, creating a long log, then pinch the seam closed. Using a sharp knife or dental floss, cut the log into twelve equal rolls and arrange them in a greased 9x13 baking dish. Cover loosely and let rise for 30 minutes while you preheat your oven to 375°F.

Bake the crowd-feeding rolls for 20–25 minutes until golden brown and the internal temperature reaches 190°F. While they cool slightly, whisk together powdered sugar, cream cheese, vanilla extract, and milk until smooth and spreadable. Drizzle the frosting generously over warm rolls so it melts into every crevice.