In a saucepan, I heat 1 cup milk, ¼ cup oil, and 6 tbsp sugar to 170–180°F (77–82°C), then cool to 110°F (43°C). In a stand mixer, I sprinkle 2¼ tsp yeast over the mixture, let it foam for 5 minutes, then add 2¾ cups flour, 1 tsp salt, and a few drops of orange food coloring. I mix with the paddle attachment, switch to the dough hook, and knead for 6–8 minutes until elastic. I transfer to a greased bowl, cover, and let rise for 1 hour until doubled for fluffy festive cinnamon treats.

In a bowl, I mix 6 tbsp softened butter, ¾ cup brown sugar, 3 tbsp black cocoa, 3 tsp cinnamon, ½ tsp salt, and 2 tsp vanilla until spreadable. I fold in ½ cup chocolate chips (if using) for rich vibrant spooky rolls.

I punch down the dough, roll it into a 12×16-inch rectangle on a floured surface, and spread the filling evenly. Starting from the long side, I roll tightly into a log and slice into 12 rolls using a knife or floss. I arrange them in a greased 9×16-inch pan, cover, and let rise for 45 minutes until puffy for perfect festive cinnamon treats.

I preheat the oven to 350°F (175°C) and bake the rolls for 20–22 minutes until soft and slightly golden. I whisk 1½ cups confectioners’ sugar, 3 tbsp milk, and 1 tsp vanilla for icing, drizzle over warm rolls, and sprinkle with Halloween sprinkles for vibrant spooky rolls.