Warm the milk until just cozy to the touch — not hot. Stir in the sugar and sprinkle the yeast on top. Let it rest for 5–10 minutes until foamy. In a large bowl (or stand mixer), combine pumpkin purée, melted butter, eggs, and pumpkin pie spice. Add the activated yeast mixture and stir until blended. Slowly add flour, a cup at a time, mixing until a soft, slightly tacky dough forms. Knead for about 5–7 minutes, until smooth and elastic.
Place the dough into a greased bowl, cover with a towel, and let it rise in a warm spot until doubled in size — usually about an hour. Once the dough has risen, gently punch it down and turn it onto a floured surface. Roll into a rectangle about 12×18 inches. Brush the surface with melted butter, then spread an even layer of brown sugar and cinnamon across the top. If you love a richer filling, add a touch of nutmeg or a sprinkle of chopped pecans.
Starting from the long side, roll the dough into a tight log and pinch the seam to seal. Slice into 12 equal rolls using a sharp knife or unflavored dental floss for clean cuts. Arrange the rolls in a greased 9×13-inch baking dish, leaving just a little space between each one. Cover loosely and let them rest for 30–45 minutes, until puffy and nearly doubled.
Preheat your oven to 350°F (175°C). Bake the rolls for about 25–28 minutes, or until golden on top and set in the center.
Pro Tip: About 10 minutes into baking, gently pour a bit of warm cream over the rolls. It keeps them soft, gooey, and bakery-perfect. (A small step I learned years ago from Tatyana’s Everyday Food — and it truly makes a difference.)
While the rolls bake, beat together softened cream cheese, butter, and vanilla extract until creamy. Slowly add powdered sugar and a splash of milk or cream until smooth and spreadable. Adjust consistency to your liking — thicker for a classic swirl or lighter for a drizzle.
Let the rolls cool for about 10 minutes before spreading the frosting over the warm tops so it melts slightly into the spirals. Serve right away — they’re best enjoyed fresh from the oven, when the kitchen smells like pure fall comfort.