Bloom your yeast by mixing active dry yeast, sugar, and warm milk together. Let it sit for 10 minutes until foamy.
In a large bowl, whisk together flour, black cocoa powder, salt, and sugar.
Add eggs, vanilla, softened butter, and yeast mixture to the dry ingredients. Mix until combined. Add black food coloring for an extra-dark dough.
Knead the dough with a dough hook attachment for 7-10 minutes until smooth and elastic. Place in a greased bowl, cover, and let rise for 1-1 ½ hours until doubled in size.
Make the filling by mixing butter, brown sugar, black cocoa powder, and salt.
Roll out the dough into a rectangle, spread the filling, then roll it up and slice into 12 rolls.
Place the rolls in a greased baking dish, pour heavy cream between them, and let rise for 1 hour.
Preheat the oven to 350°F. Bake the rolls for 20-25 minutes.
Make the cream cheese frosting by mixing softened butter, cream cheese, black cocoa powder, powdered sugar, and milk. Add black food coloring if desired.
Let the rolls cool for 5 minutes, then spread the frosting on top. Decorate with candy eyeballs and Halloween sprinkles. Serve and enjoy!