Prepare the Dough: In a small bowl, dissolve the active dry yeast in warm milk. Allow it to sit for about 5-10 minutes until frothy. In a large mixing bowl, combine the flour, sugar, salt, ground cinnamon, and ground nutmeg.
Mix Wet Ingredients: In a separate bowl, whisk together the pumpkin puree, melted butter, eggs, and vanilla extract. Once the yeast mixture is frothy, add it to the wet ingredients.
Combine Mixtures: Pour the wet mixture into the flour mixture and mix until a soft dough forms. If the dough is too sticky, add a bit more flour, one tablespoon at a time.
Knead the Dough: Lightly flour a clean surface and knead the dough for about 5-7 minutes until it is smooth and elastic. Form it into a ball and place it in a greased bowl, covering it with a clean kitchen towel. Let it rise in a warm place for 1 to 1.5 hours, or until doubled in size.
Make the Filling: In a small bowl, mix together the brown sugar and ground cinnamon. Set aside.
Roll Out the Dough: Once the dough has risen, punch it down and transfer it to a lightly floured surface. Roll it out into a rectangular shape, about 0.5 inches thick.
Add the Filling: Spread the softened butter evenly over the dough and sprinkle the cinnamon-sugar mixture all over, leaving a small border around the edges.
Roll and Cut: Starting from the longer edge, carefully roll the dough into a tight log. Pinch the seam to seal it. Cut into 12-15 even pieces and place them cut-side up in a greased 9x13-inch baking dish.
Second Rise: Cover the rolls with a kitchen towel and let them rise again for 30-45 minutes until they puff up.
Bake: Preheat the oven to 350°F (175°C). Bake the rolls for 25-30 minutes or until they are golden brown and cooked through. Remove from the oven and let cool slightly.
Prepare the Glaze: Whisk together powdered sugar, milk, and vanilla extract in a small bowl until smooth. Adjust the consistency with more milk or powdered sugar if necessary.
Glaze and Serve: Drizzle the glaze over the warm rolls and serve them warm. Enjoy your delicious Cinnamon Sugar Pumpkin Rolls!