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Step 1
Warm the milk in a bowl in the microwave for just about 1 minute until it is warm. Pour it into a large bowl.
Step 2
Add in the sugar and salt, then stir the mixture. The mixture should measure about 105-110 degrees F in order activate the yeast. Add 1 package of instant yeast right to this milk. Allow the yeast to sit for 3-5 minutes until the yeast is slightly frothy and activated.
Step 3
Add the softened (almost melted) butter, pumpkin, pumpkin pie spice, cinnamon and vanilla. Stir this gently until it is all blended together.
Step 4
Gradually add in the flour, 1 cup at a time. Add in the last 1/2 a cup and start to knead the dough with your hands until the last 1/2 cup of flour is incorporated in. Turn the dough out onto a floured surface and continue to knead the bread for about 7 minutes until it is smooth and elastic. Add a bit more flour as you need to during kneading. The dough should still feel sticky, but it will not stick to your hands.**
Step 5
Place this dough in a greased bowl and cover it. Allow the dough to rise in a warm place until it has doubled, about 30-40 minutes.
Step 6
While the dough is rising, prepare the cinnamon filling. In a medium bowl, combine the soft butter, brown sugar, spices and pumpkin puree, mixing until well combined. Set aside.
Step 7
Sprinkle a pastry mat generously with flour. Turn out the dough onto the pastry mat and sprinkle the top of the dough with additional flour. Flour a rolling pin and roll the dough to about a 24x15" rectangle. (the size of the rectangle can vary...it does not have to be exact!)
Step 8
Use a rubber spatula to smooth the pumpkin filling over the whole dough rectangle.
Step 9
Starting on the long end, roll the dough up tightly jelly roll style. Cut into 15 slices and place in a greased 9x13 baking pan. If you have a slightly larger baking pan, that would be good to use. You can also use two round or square pans.
Step 10
Cover the pan and allow the rolls to rise for 20 minutes or until nearly double.
Step 11
Preheat the oven to 350 degrees. Warm the heavy cream until the chill is off. Don't make it hot...you just don't want it cold. It should be warm to the touch.
Step 12
Once the rolls have risen, pour the heavy cream over the top of the rolls, allowing it to soak down in and around the rolls.
Step 13
Bake at 350 degrees for 25-28 minutes, until the rolls are lightly golden brown and the center rolls are cooked through. Note...the time will vary based on how big the rolls are, what type of pan, how close the rolls are packed, etc.
Step 14
If the rolls are getting too brown, place a piece of foil over the rolls during the last part of baking.
Step 15
Allow the rolls to cool slightly.
Step 16
In a large bowl, combine the softened cream cheese and butter using a hand mixer. Blend well.
Step 17
Add in vanilla extract, cinnamon and the powdered sugar. Beat until combined.
Step 18
Spread the frosting over the cooled rolls.
Step 19
Store in an airtight container.