Combine your bread flour, Dutch cocoa powder, light brown sugar, salt, instant yeast, eggs, and warm whole milk in the bowl of your stand mixer or a large mixing bowl if you’re mixing by hand.
Start mixing on low speed until a soft, slightly sticky dough begins to form. Then, add half of the softened butter and continue mixing until it’s mostly absorbed. Add the rest of the butter and mix on low to medium speed for 5 to 8 minutes until your dough turns silky smooth and soft to the touch.
Roll the dough into a ball and put it into a bowl. Cover it with a towel and find a warm, quiet spot—near a sunny window or inside a turned-off oven with the light on. Let the dough rise for about two hours or until it doubles in size.
While the dough rises, prepare a 9-inch square pan by lining it with parchment paper, so your rolls have a cozy spot to rest before baking.
For the filling, set up a double boiler by simmering water in a pot. In a heat-safe bowl over simmering water, melt the butter and chocolate, stirring until glossy and smooth. Stir in the cocoa powder, espresso powder, and cinnamon, then allow the mixture to cool slightly until it’s warm but not hot.
After the dough has risen, gently punch it down and roll it out on a lightly floured surface into a rectangle. Smooth the chocolate filling across the dough, keeping a small margin along the edges so it stays inside when you roll it up. Roll the dough tightly from one short side, sealing the seam by pinching it closed. Use a serrated knife to cut the log into 8 to 10 equal pieces.
Place the rolls cut side up in the prepared pan, arranging them close enough to touch but not overcrowded. Cover loosely and let them rise for another 30 minutes until puffed. Heat the oven to 350°F (175°C) and bake the rolls for around 20 minutes, until the edges are golden and the filling’s glossy finish fades.
Beat cream cheese and powdered sugar together until smooth and airy. Add cocoa, vanilla, and milk, blending until the frosting reaches a creamy, spreadable texture. Spread this luscious frosting generously over the warm rolls, then enjoy every rich, gooey bite!