Activate yeast. Sprinkle yeast over warm water, stir in teaspoon for sugar. Let sit until foamy, about 5-7 minutes.
If mixture doesn't bubble, your yeast is dead. Start over with a fresh batch before you waste the rest of your ingredients!
Mix dough. In the bowl of a stand mixer, whisk together yeast mixture, milk, brown sugar, egg, egg yolk, and pumpkin puree. Use dough hook attachment and gradually mix in flour and salt (reserve about 1 cup of flour). Continue to knead on low speed while adding softened butter one tablespoon at a time. Add remianing 1 cup flour and knead until sough is smooth and pulls cleanly from the sides of the bowl.
First rise. Transfer dough to a lightly greased bowl. Cover with plastic wrap and let sit at room temperature for about an hour until doubled.
Roll it out. Punch down dough and roll into a 20x14-inch rectangle.
Filling:
Fill it. In a small bowl, mix together softened butter and pumpkin puree until smooth Add in sugar, cinnamon, cocoa powder, and salt. Spread mixture over the entire surface of rolled out dough. Sprinkle chopped chocolate on top.
Slice and roll. Measuring at the long side, divide dough into 12 equal strips (about 1 ½-inches wide). Roll dough into a spiral. Arrange in a greased 9x13-inch baking pan.
Second rise. Cover. Let rest for 30-45 minutes at room temperature until rolls are puffy. Meanwhile preheat oven to 350℉.
Bake. Uncover. Place rolls in the center rack of preheated oven. Bake for 30-35 minutes, rotating midway, until golden on top and internal temperature registers at least 185℉. Cool 10 minutes before frosting.
Frosting:
Frost. Sift together confections sugar and cocoa powder. Add salt and milk. Stir until smooth and thick. Spread generously over warm rolls.
Notes
Best enjoyed warm.
Unfrosted rolls keep well covered at room temperature for 24 hours. Once frosted, enjoyed within 10-12 hours for best texture.
Store leftovers in a covered container in the fridge for up to three days. Reheat in a toaster oven. Or, reheat in the microwave for 15-20 second intervals alongside a small cup of water to keep rolls from drying out (or getting gummy).
See blog post for make-ahead option.
Ingredients:
Recommend using chocolate block bar (Trader Joe's has great options). Chocolate chips work, but they will create uniform chip shapes instead of irregular pockets of gooey chocolate.