First, warm the milk in the microwave for about 60 seconds or until it reaches around 105°F-110°F. Use a cooking thermometer to ensure it’s not too hot, as excessive heat can kill the yeast. If it’s too hot, let it cool slightly before proceeding. Set the warm milk aside.
2/3 cup milk
Once the milk mixture is at the right temperature, pour it in the stand mixer bowl, stir in 1 tablespoon of granulated sugar and sprinkle the yeast on top. Stir and let it bloom for about 5 minutes.
2 tsp active dry yeast
In a separate medium bowl, combine the flour, the other tablespoon of granulated sugar, brown sugar, pumpkin pie spice ad the salt. Whisk until fully combined and set aside.
2 & 2/3 cup all purpose flour, 2 tbsp granulated sugar, 2 tbsp brown sugar, 2 tsp pumpkin pie spice, 1/2 tsp salt
Add in the melted butter vanilla, egg, and pumpkin puree to the milk mixture and mix using a paddle attachment.
3 tbsp butter, 1 tsp vanilla, 1 large egg, 1/3 cup pumpkin puree
Add in the flour mixture, change the mixer attachment to the hook attachment and knead the dough for 7-10 minutes. The dough should pull away from the sides of the bowl. if the dough looks too wet add in 1 tbsp of flour at a time until the dough still looks slightly wet but pulls out of the sides of the bowl. Remove the dough from the stand mixer bowl, form it into a ball using your hands and place it back in a lightly greased bowl. Cover with a damp towel and let it sit somewhere warm for 30 minutes.
Make the cinnamon roll filling
In a small bowl, mix the brown sugar, pumpkin pie spice, and the cinnamon together until well combined.
1/2 cup brown sugar, 1 tbsp cinnamon , 1 tsp pumpkin pie spice
Let's make some cinnamon rolls!
Once the pumpkin cinnamon roll dough is ready, place it on a floured work surface and roll it using a floured rolling pin. You want to create a large rectangle of about 14.5 x12 inches in size. Use an offset spatula or your hand to spread the softened butter onto the entire surface of the rolled out dough. Sprinkle the dough evenly with the brown sugar mixture, then gently pat it down into the butter.
1/4 cup butter
Starting at the 14.5-inch edge, tightly roll up the dough until you get to the end then gently pinch it to seal the edges if you'd like. a more clean look. Now using a large piece of floss or a sharp knife, slice off a small piece of both edges of the roll ( about 1/4 inch on each end) Cut the remaining dough into 9 even slices.
Place those cinnamon rolls into a buttered 8x8 inch baking pan, cover with plastic wrap and let them rise for 15-20 minutes or until they doubles in size. While the cinnamon rolls are rising, heat up the oven to 350F.
Once the rolls are done rising, pour the heavy cream over them and bake in the oven for 22-28 minutes, or until the rolls are golden brown and cooked through. Once they're baked, let them cook for 5 minutes, spread the homemade frosting on top and serve.
Make the frosting
While the cinnamon rolls are still baking, whisk the cream cheese, butter, maple syrup, powdered sugar, and the vanilla bean paste together in a small bowl. If the frosting seems too thin add 1tbsp at a time of powdered sugar and stir. If it seems too thick add 1 tbsp of milk at a time ad stir.
1/3 cup heavy cream, 4 oz Cream cheese, 3 tbsp Maple syrup, 4 tbsp Butter, 1/3 cup Powdered sugar, 1 tsp Vanilla bean paste
Notes
These are best warm, straight out of the oven. Store leftovers in an airtight container in the fridge for up to 5 days and reheat in the microwave for 15 to 20 seconds.To make them ahead, assemble through shaping, cover the pan tightly, and refrigerate overnight. Let the pan sit at room temperature for about an hour before baking, then add 2 to 3 minutes to the bake time.